What would you have done differently on your first STR?

What would you have done differently on your first STR?

Member since 2018 · 19 posts · 10 votes

I'm analyzing deals for my first short term rental. I'm doing all the research: podcasts, books, webinars, articles, etc. along with finding markets where I should have an easier time finding a cleaner and handyman. I'm pretty savvy with Excel so I've built a spreadsheet that does the ROI, etc. and am working on some formulas that spit out average occupancy/rates when I dump in data from PriceLabs. I'm also in the process of building a checklist/shopping list for items I may or may not need (depending on what conveys).

My next steps are to connect with a realtor and lender.

But I don't know what I don't know. So, for those that have been down this road before, what did you learn from your first STR purchase that you wish you had known before you jumped in? Or what would you do differently with the benefit of hindsight?

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Investor · Flowery Branch, GA · Member since 2019 · 413 posts · 412 votes
5y

I would have stopped analyzing and started critical path items sooner. Until you get on the ride you don’t know what you’re in for. Best to learn by making mistakes. The more those mistakes cost you the better lesson you learn unfortunately.

And have ample reserves just in case.

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  • Investor · Flowery Branch, GA · Member since 2019 · 413 posts · 412 votes
    5y

    I would have stopped analyzing and started critical path items sooner. Until you get on the ride you don’t know what you’re in for. Best to learn by making mistakes. The more those mistakes cost you the better lesson you learn unfortunately.

    And have ample reserves just in case.

  • Investor · Placitas, NM · Member since 2019 · 105 posts · 61 votes
    5y

    Standard homeowners insurance or even landlord insurance is not designed for STRs. The number of coverage providers is much smaller than for the regular types of insurance for investment properties.  And from my experience so far, it is more expensive.  But I think the coverage for STRs is a must, given the potential for liability with guests rotating through frequently.  Look for 20 - 30% higher premiums than typical LTR insurance.  Just my experience so far, limited though it be.

  • Investor · The worst town to live in, KS · Member since 2016 · 4k+ posts · 4k+ votes
    5y

    Have internet and a gas/charcoal grill.  That was the first 2 things my first 2 tenants asked for 10 years ago.

  • Property Manager · Nashville & Salt Lake City · Member since 2015 · 78 posts · 20 votes
    5y

    You can find STR checklist of furnishings & supplies here: https://home-havens.com/shop-t... Also, you can recommend travel insurance to reduce cancellation requests. https://www.bnbbosses.com/blog...

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Joshua Strickland:

    I would have stopped analyzing and started critical path items sooner. Until you get on the ride you don’t know what you’re in for. Best to learn by making mistakes. The more those mistakes cost you the better lesson you learn unfortunately.

    And have ample reserves just in case.

    I can definitely be guilty of analysis paralysis. I agree a lot can be learned from mistakes. I'm not afraid to make them and I know I'm not immune to them. Just looking to learn the lessons without making too many myself. Good encouragement to not sit in the analysis too long though!

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Randy Dubiskas:

    Standard homeowners insurance or even landlord insurance is not designed for STRs. The number of coverage providers is much smaller than for the regular types of insurance for investment properties.  And from my experience so far, it is more expensive.  But I think the coverage for STRs is a must, given the potential for liability with guests rotating through frequently.  Look for 20 - 30% higher premiums than typical LTR insurance.  Just my experience so far, limited though it be.

    This is great feedback. Thank you. Do you have an insurance broker you go through for STR properties? I hadn't really considered this.

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Paul Sandhu:

    Have internet and a gas/charcoal grill.  That was the first 2 things my first 2 tenants asked for 10 years ago.

    Are you nearby to your STRs? I had thought about this, but it will be an out-of-state property for me, so I won't be around much to check the status of the propane. I guess I could have a couple tanks available and make sure they are replenished the couple times of year that I make the trip. How do you handle it?

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Tanner Morrill:

    You can find STR checklist of furnishings & supplies here: https://home-havens.com/shop-t... Also, you can recommend travel insurance to reduce cancellation requests. https://www.bnbbosses.com/blog...

    Thank you for making my life a lot easier with that furnishings/supplies list! And great tip on the travel insurance. My family just had to cancel an Airbnb booking late ourselves recently so I definitely know the value of rental insurance. I haven't seen many hosts offer it, but I could see the benefit in being upfront about it in your listing. Thanks!

  • Investor · Placitas, NM · Member since 2019 · 105 posts · 61 votes
    5y

    You could try an insurance broker recommended by your realtor. They should be licensed in the state you are purchasing your STR. I would recommend direct contact with Proper Insurance or CBIZ, but check on some of the brokered firms as well.

  • Investor · The worst town to live in, KS · Member since 2016 · 4k+ posts · 4k+ votes
    5y
    Originally posted by @Jason Wolohan:
    Originally posted by @Paul Sandhu:

    Have internet and a gas/charcoal grill.  That was the first 2 things my first 2 tenants asked for 10 years ago.

    Are you nearby to your STRs? I had thought about this, but it will be an out-of-state property for me, so I won't be around much to check the status of the propane. I guess I could have a couple tanks available and make sure they are replenished the couple times of year that I make the trip. How do you handle it?

    I'm 7 minutes away from my furthest STR. If you look back at my old posts, there is a picture of about 15 of my propane tanks.

  • Walnut Creek, CA · Member since 2020 · 285 posts · 318 votes
    5y

    @Jason Wolohan a couple of things:

    • Wish I had known how much of a pain neighbors can be. It's not their fault, living next to an Airbnb isn't the most fun place to be. Just make sure you do all you can to get to know your neighbors so they don't try to ruin the guest experience or jeopardize your STR permit.
    • Wish I had known how much a reliable handyman and cleaner means to your business. Find the best ones you can and treat them like a million bucks, because they will be the reason you succeed or fail.
    • Wish I had known how much good communication can help save a 1-star experience. We've certainly had some hiccups with guests (including 2 chairs breaking in 1 reservation), but because we stayed on top of communication we were able to preserve a 5-star experience. Remember this is a hospitality business, so the faster you can respond to your guests' needs the better you'll do.

    Good luck and feel free to DM me with any questions!

  • Rental Property Investor · Lancaster, PA · Member since 2018 · 56 posts · 57 votes
    5y
    Originally posted by @Jason Wolohan:
    Originally posted by @Paul Sandhu:

    Have internet and a gas/charcoal grill.  That was the first 2 things my first 2 tenants asked for 10 years ago.

    Are you nearby to your STRs? I had thought about this, but it will be an out-of-state property for me, so I won't be around much to check the status of the propane. I guess I could have a couple tanks available and make sure they are replenished the couple times of year that I make the trip. How do you handle it?

    Stuff like this I'll have my cleaner or handyman check and replace as needed. If you put in a charcoal grill they can just provide their own charcoal.

    Internet is especially important now with the rise remote work, you'll have folks that want to work from your STR during the week and require fast, reliable internet.

  • Investor · Metro East of St. Louis (Illinois) · Member since 2016 · 255 posts · 211 votes
    5y

    @Jason Wolohan my first thought after reading your post was..."he's ready. time to get off the sidelines and execute!"  Much like @Joshua Strickland said.

    You are gonna mess things up; it is inevitable. On my first STR, I ripped out a perfectly functional shower for a unit that makes $99/night and tried to tile it. Long story short, it cost thousands to fix and looks worse now than it did when I started. It would have been a perfect BRRRR (no cash left in the deal), but I ended up with $10K left in it...it nets $10K/yr.

    In other words, just go for it.  Your mistakes in the beginning will cost you money, but not as much money as waiting another 6 months to get started.

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Jimmy Woodard:

    @Jason Wolohan a couple of things:

    • Wish I had known how much of a pain neighbors can be. It's not their fault, living next to an Airbnb isn't the most fun place to be. Just make sure you do all you can to get to know your neighbors so they don't try to ruin the guest experience or jeopardize your STR permit.
    • Wish I had known how much a reliable handyman and cleaner means to your business. Find the best ones you can and treat them like a million bucks, because they will be the reason you succeed or fail.
    • Wish I had known how much good communication can help save a 1-star experience. We've certainly had some hiccups with guests (including 2 chairs breaking in 1 reservation), but because we stayed on top of communication we were able to preserve a 5-star experience. Remember this is a hospitality business, so the faster you can respond to your guests' needs the better you'll do.

    Good luck and feel free to DM me with any questions!

    Thanks Jimmy. Sound advice! I think you probably don't really know how the neighbors will perceive you once they learn you're doing short term rentals, but they'll find out either way so I'd assume the best thing to do is to build rapport. Hopefully they'd then become another set of eyes on the property for you as well.

    Kudos on saving the review. Do you use systems for communication automation in addition to just being generally available during the course of their stay? And on that note, at what point in the stay do you find that guests most likely have an inquiry? I'm sure there are random questions, but is there is a pattern?

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Jason Stoltzfus:
    Originally posted by @Jason Wolohan:
    Originally posted by @Paul Sandhu:

    Have internet and a gas/charcoal grill.  That was the first 2 things my first 2 tenants asked for 10 years ago.

    Are you nearby to your STRs? I had thought about this, but it will be an out-of-state property for me, so I won't be around much to check the status of the propane. I guess I could have a couple tanks available and make sure they are replenished the couple times of year that I make the trip. How do you handle it?

    Stuff like this I'll have my cleaner or handyman check and replace as needed. If you put in a charcoal grill they can just provide their own charcoal.

    Internet is especially important now with the rise remote work, you'll have folks that want to work from your STR during the week and require fast, reliable internet.

    I haven't gotten to the point of finding a cleaner yet, but for you, do you have a specific individual(s) or a company? My thought behind the question is this: if it's a company, how will one cleaner to the next know the unique tasks for your property that might be different than the other properties they clean?

    My thought was to have a "unique" checklist in the cleaning/supplies closet. Not to micromanage - they know how to clean a house - but for the unique things (like checking the propane tanks, replenishing the welcome basket, or whatever else might be different than a standard cleaning). Has anyone done this? 

  • Walnut Creek, CA · Member since 2020 · 285 posts · 318 votes
    5y

    Yes, build rapport up front and let them know your intentions so it doesn't come as a surprise later.

    I use Your Porter to automate my messages to guests. Most of your guest questions will come in the first 24 hours since it's new territory for them. Granted, I have an extensive house manual that answers most questions, but there will always be fringe questions that people need help with. Or if something goes wrong, they'll certainly let you know :)

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Alex S.:

    @Jason Wolohan my first thought after reading your post was..."he's ready. time to get off the sidelines and execute!"  Much like @Joshua Strickland said.

    You are gonna mess things up; it is inevitable. On my first STR, I ripped out a perfectly functional shower for a unit that makes $99/night and tried to tile it. Long story short, it cost thousands to fix and looks worse now than it did when I started. It would have been a perfect BRRRR (no cash left in the deal), but I ended up with $10K left in it...it nets $10K/yr.

    In other words, just go for it.  Your mistakes in the beginning will cost you money, but not as much money as waiting another 6 months to get started.

    Thanks for the vote of confidence Alex! I've got a call with a realtor today in a market I've narrowed it down to and a mortgage broker tomorrow that will hopefully be able to get me a 10% down vacation property loan.

    Nice net on that property! I know all properties/markets are different, but our one LTR that (only) nets us $6,276 annually is one of the reasons why we're going STR next (it's a good ROI for us, but I think we can do better with STR). We like to travel ourselves, my wife loves the idea of hospitality and helping others enjoy their vacation, and I like the increased ROI. So it seems like it'll be fun.

  • Member since 2018 · 19 posts · 10 votes
    5y
    Originally posted by @Jimmy Woodard:

    Yes, build rapport up front and let them know your intentions so it doesn't come as a surprise later.

    I use Your Porter to automate my messages to guests. Most of your guest questions will come in the first 24 hours since it's new territory for them. Granted, I have an extensive house manual that answers most questions, but there will always be fringe questions that people need help with. Or if something goes wrong, they'll certainly let you know :)

    I haven't heard of Your Porter. I'll have to check that out.

    A slightly different topic, but related to the reviews. Do you have a travel log or book in your houses that guests can write in? As a guest myself, I like reading through previous guests' comments because this is often times where people reference a good restaurant or hike or whatever so I can get some good ideas. But I'm curious if having one of those logs 1) competes with your online reviews (i.e. are guests who leave their "review" in your travel log less likely to review you online?), 2) are the guests leaving comments in the log that you can't respond to in a timely manner because you only visit the property every once-in-awhile?

  • Rental Property Investor · Lancaster, PA · Member since 2018 · 56 posts · 57 votes
    5y
    Originally posted by @Jason Wolohan:
    Originally posted by @Jason Stoltzfus:
    Originally posted by @Jason Wolohan:
    Originally posted by @Paul Sandhu:

    Have internet and a gas/charcoal grill.  That was the first 2 things my first 2 tenants asked for 10 years ago.

    Are you nearby to your STRs? I had thought about this, but it will be an out-of-state property for me, so I won't be around much to check the status of the propane. I guess I could have a couple tanks available and make sure they are replenished the couple times of year that I make the trip. How do you handle it?

    Stuff like this I'll have my cleaner or handyman check and replace as needed. If you put in a charcoal grill they can just provide their own charcoal.

    Internet is especially important now with the rise remote work, you'll have folks that want to work from your STR during the week and require fast, reliable internet.

    I haven't gotten to the point of finding a cleaner yet, but for you, do you have a specific individual(s) or a company? My thought behind the question is this: if it's a company, how will one cleaner to the next know the unique tasks for your property that might be different than the other properties they clean?

    My thought was to have a "unique" checklist in the cleaning/supplies closet. Not to micromanage - they know how to clean a house - but for the unique things (like checking the propane tanks, replenishing the welcome basket, or whatever else might be different than a standard cleaning). Has anyone done this? 

    I have an individual cleaner so I get her to do all sorts of odds and ends when she goes over. She has other folks that clean with her but she trains them up.

    I also have a very specific checklist for turnovers and cleaning. I don't think that's micromanagement, it actually makes expectations very clear and concise, and it makes the process easier if you ever switch cleaners.

  • Walnut Creek, CA · Member since 2020 · 285 posts · 318 votes
    5y

    We don't have one but if anyone else has insights here I would love to hear it.

  • Rental Property Investor · Denver, CO · Member since 2019 · 78 posts · 66 votes
    5y

    @Jason Wolohan

    - Underwrite it conservatively (and if the numbers are better than projected you’ll be pleasantly surprised).

    - Don't over improve it. It's easy to buy expensive items and make improvements that don't yield much ROI. We went nuts on our first STR (as if we were going to live there). Still cash flows well though…see first bullet.

  • Gary NelsonBusiness Member
    Real Estate Agent · Branson, MO · Member since 2016 · 141 posts · 93 votes
    5y

    @Jason Wolohan do you have a short-list of markets you’re considering?

    Gary Nelson Real Estate, EXP Realty, LLC553 Reviews
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