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All Forum Posts by: Kevin G.

Kevin G. has started 22 posts and replied 64 times.

Quote from @Tyler Gibson:
Quote from @Kevin G.:

Hello everyone!

I am very interested in investing in STRs in Kissimmee, FL or in LTRs in Tampa. I currently live in California and am wondering if it is feasible to invest so far out of state. How much would I realistically need to be "boots on the ground" to pull this off? I know out-of-state investing gets asked about a lot, but I would love to learn from people who are actually doing it in Florida.

I am considering Florida due to its lower barrier of entry for someone like me from California. I had originally thought of investing in the SoCal and San Diego markets, but the overall cash needed is too high.

For STRs, I have thought about Kissimmee due to its strong demand and close proximity to Disney World. My plan is to find a 4-bedroom single-family home with a pool or in a community that has a pool, which needs some moderate renovations to build some instant equity. Then, I would design it to have a nice Disney theme to attract guests. The hard part is being in California to make this happen.

Another option for me was to invest in the strong market of Tampa, FL for an LTR. I don't know much about the market, but from what I've gathered so far, homes have appreciated drastically and continue to appreciate. I'd look at either SFH or multi-family units in this area to rent out.

Any advice would be greatly appreciated! Thank you.


Hello, when considering investing in the Disney area a couple of things to keep in mind. The best performing properties are five plus bedrooms and are highly themed out. You do not have to be that much boots on the ground in order to own and operate these, especially if you hire a great property manager. Disney short-term rentals require you to have a world-class operation along with world class theming and design. I also suggest you buy a property in one of the resort style communities while this will have a higher HOA cost it will allow you to use all the great amenities that they have such as the pools, clubhouse, fitness center, and other great amenities that some of these resorts offer as part of your marketing material.

Long-term rental opportunities can still be found in Central Florida including areas between Tampa and Orlando.

Hi Tyler! Thank you for the great information. However, I must respectfully disagree with your statement that SFH with 3 to 4 bedrooms would not be profitable. When I use multiple factors to determine if a property would be a good investment for me, I find that there are quite a few properties that offer both cash flow and appreciation potential. While I understand that this may be more limited that a larger home, my research has shown that it can still be done.

Although I do agree that a 5 bedroom property would be ideal for investment purposes, I have been using metrics such as Airdna, Awning, Datarabbu, and DealCheck to analyze and evaluate my properties in order to get a better understanding of whether or not they will be profitable.

Maybe I'm thinking more long-term, but a single-family home seems to be a better option for appreciation compared to a condo.

Thoughts?


Hello everyone!

I am very interested in investing in STRs in Kissimmee, FL or in LTRs in Tampa. I currently live in California and am wondering if it is feasible to invest so far out of state. How much would I realistically need to be "boots on the ground" to pull this off? I know out-of-state investing gets asked about a lot, but I would love to learn from people who are actually doing it in Florida.

I am considering Florida due to its lower barrier of entry for someone like me from California. I had originally thought of investing in the SoCal and San Diego markets, but the overall cash needed is too high.

For STRs, I have thought about Kissimmee due to its strong demand and close proximity to Disney World. My plan is to find a 4-bedroom single-family home with a pool or in a community that has a pool, which needs some moderate renovations to build some instant equity. Then, I would design it to have a nice Disney theme to attract guests. The hard part is being in California to make this happen.

Another option for me was to invest in the strong market of Tampa, FL for an LTR. I don't know much about the market, but from what I've gathered so far, homes have appreciated drastically and continue to appreciate. I'd look at either SFH or multi-family units in this area to rent out.

Any advice would be greatly appreciated! Thank you.

Post: 1st time STR purchase question

Kevin G.Posted
  • Investor
  • Bay Area, CA
  • Posts 66
  • Votes 41

Hey Matt! I would like to add to what others have said and suggest considering paying for a city subscription on Airdna to get a more accurate idea of the area's income potential. This service provides real-time occupancy data, average daily rates, and allows you to view other properties, among other things. I am confident that you can increase your income, and identifying what is holding it back, such as subpar design or location, can help. Additionally, there are other great websites that offer free information, like Awning.com or Data.rabbu.com.

My strategy is to use all three sites and gather accurate information on occupancy rates, daily rates, etc. to make an informed decision about investing in the property. As others have mentioned, using as many listing websites as possible can also help.

It's important to also consider the local real estate market and trends. Look at the demand for vacation rentals in the area and see if it's increasing or decreasing. This can give you an idea of the potential for growth in the future. Additionally, consider any unique features or amenities that your property may have that could attract more guests. Don't be afraid to invest in upgrades or renovations that could increase the value of your property and attract more guests. Good luck with your new STR!

Quote from @Melissa Nash:

I own 5 STR's in SoCal. this is a GROWTH strategy, maybe not crazy high cashflow. If your strategy is about saving taxes, gaining long term wealth through equity, and being able to use the property for yourself while paying for the property and sometimes profiting- then yes- SOCAL markets do work. But you have to be unique and stand out. The properties that profit the highest are really really cool or do outstanding amenities and design. You have to be in the 10% of desired properties in the area to make $. Regulations will be your biggest battle.... no one goes to desert hot springs by the way. I bought/and sold a property there and its dead dead right now. Palm Springs just passed a new law only 26 stays per year allowed, and Big Bear requires an onsight PM- that will kill your ROI, Arrowhead guests can't use docks, beaches or lake- that dropped demand. Joshua tree is saturated- but if you are really really unique and funky you can make it work. If I were to buy another STR right now in Socal, I would do something unique like a campsite, or a glamping tent or something like that that is affordable- caters to 2 guests and something memorable and insta worthy. Oceanside is a great market too......

For Oceanside what neighborhoods would you recommend looking at for a STR? Does it have just as high occupancy as San Diego? I’ve been wanting to invest in an STR in San Diego and continue buying more if it works out but others have advised against this because of the new STR laws in San Diego. Oceanside seems a little out of the way for tourists who want to do things in San Diego as well. 

@Dan H. Thank you for sharing, Dan. It seems like the 30+ day rental is the best option for you and your family, as it still allows you to visit the property. I understand your concerns, though! After doing some research, I discovered that San Diego only permits one short-term rental at a time within the city. This means that you can only obtain one license. Unfortunately, this is bad news for me, as I had planned to expand if the first property was successful as a STR. I'm now considering whether the 30+ day rental or long-term rental route is better. These regulations are causing significant difficulties for both investors and guests!

@Dan H. 

Ah, ok. That makes a lot of sense now. I'm sorry to hear about what happened to your property. It's a huge bummer, and I can totally understand your frustration, especially as a tax-paying citizen. It's unfortunate that politics are getting in the way of things. What are your plans for the property moving forward? If you can't do short-term rentals (STR) or long-term rentals (LTR), what makes sense? Are you currently on the waitlist for a Tier 4 license?

I also agree with what you're saying about STRs outside of Mission Beach. I don't believe there are as many as people think. Sure, there are a lot, but the city was expecting around 16,000, and that hasn't been the case. If I'm wrong, why wouldn't people just apply for a Tier 3 license if they're still available? Maybe they're planning to stop doing STRs after these new restrictions. Who knows? As an aspiring host in San Diego and frequent guest of Airbnb in the area, I love visiting. So, I'm hoping things don't get worse.

Quote from @Dan H.:
Quote from @Kevin G.:
Quote from @Bruce Woodruff:

Why San Diego? Once you sub out all the tasks is there really enough $$ to justify it? Like @John Underwood said, what about other, less discovered areas in other states?

Have you done a spreadsheet and run your numbers?

After analyzing properties in SD it defiantly makes sense and cash flows really well. But this all dependent on finding the right deal, right neighborhood etc. I’m picking San Diego because it has a high occupancy rate and year around weather is perfect. I’m skeptical about picking less known areas because then I run the risk of having a low occupancy rate. Especially if not many people are traveling to that location. 

There is some fees to start like applying for your license , pay taxes, etc but it still seems worth it. 

My fear is that San Diego is not finished limiting/restricting STRs. I could be that I am jaded because my STR that operated legally since 1999and paid all its occupancy taxes did not get an STR permit in spite of having maximum lottery entries (maximum Lottery entries was for STRs over 5 years old).

If the city can eliminate an STR that has operated legally for 23 years, it certainly can change the rules to further restrict/limit STRs.

Beware of STRs in markets that the politicians are anti STR. by the way this str quota occurred in spite of the politicians being afraid to place on ballot. The counsel had previously passed an anti STR ordinance. Signatures were gathered to place on the ballot. Counsel pulled that regulation.

It is my belief further regulations are likely.  I recommend a different market.  

Good luck


Are you not able to apply for a new STR license through the city now in the "Tier 3" category? It sounds like there is still plenty of spots left. One news article that I read stated that they expect not everyone who owns a STR applied for the license and will be operating their STR illegally. We shall see.

Thank you for the advice. When I do the numbers, look at regulations, occupancy rate, etc. It still sounds like a good plan. I am also picking an area that I can easily get to - which is important to me. 

I do agree with you though that further regulations are to come, sadly, but if you have a license and are operating legally I don't see why you'd get even further punished for that. 

Quote from @Nicholas Coulter:

@Bruce Woodruff I agree with you 100%. If the opportunity is there to HH in a place like this I consider it a win win. Likely with these prices and ROIs the HH is the best strategy to get a higher ROI. If not maybe out of state makes sense. I have looked into out of state outside of my HH plan in SD. If you ever come visit I'll try and convince you to move back!

House hacking would always be an awesome deal. Even though I’d love to move down to San Diego I don’t think I’ll be able to just yet. I would still need to work up here in the Bay Area. I’m not against mega commuting but it would be tough. 
Quote from @Lauren Kormylo:
Quote from @Erik Acheff:

Carlsbad, Oceanside, and Escondido are county areas and would not be a part of the San Diego City STR applications. I live in Carlsbad, and they have strict guidelines for STR properties. You must get a business license and notify neighboring properties. While the short-term vacation rental unit is rented, a local contact person needs to be available 24 hours per day, seven days per week, to respond within 45 minutes to complaints regarding the condition, operation, or conduct of occupants of the short-term vacation rental unit or their guests. If you get three citations in 24 months, they revoke your license, and you can not renew for 36 months. Most cities have specifics like this for STR properties. I would proceed with caution. I am a property manager, but I stay away from STR properties.


 These requirements are common in many cities all over the country now.  Including Sedona, Scottsdale, and Paradise Valley, all in Arizona.  And these 3 cities go farther with the requirement of a background check for the main guest.  In addition, Scottsdale has a limit of only 6 adults per house, no matter how large it is.

These restrictions have nothing to do with red/blue states, they are the result of NIMBYs, who are all over.  

That’s unfortunate to hear. San Diego does have some strong restrictions as well but with their tier system it sounds like there is still plenty of applications left for STR in the city. Not all cities outside of San Diego have such strong restriction either. 
Quote from @Bruce Woodruff:

Why San Diego? Once you sub out all the tasks is there really enough $$ to justify it? Like @John Underwood said, what about other, less discovered areas in other states?

Have you done a spreadsheet and run your numbers?

After analyzing properties in SD it defiantly makes sense and cash flows really well. But this all dependent on finding the right deal, right neighborhood etc. I’m picking San Diego because it has a high occupancy rate and year around weather is perfect. I’m skeptical about picking less known areas because then I run the risk of having a low occupancy rate. Especially if not many people are traveling to that location. 

There is some fees to start like applying for your license , pay taxes, etc but it still seems worth it.