All Forum Posts by: Ryan Osborne

Hello all, new investor here! I am working on rehabbing some smaller cottages in northern Michigan, the plan is to put them all on the STR market once they are complete. It seems to me sites like AirDNA and other revenue estimators for STR's seem to be giving me what I feel is an unrealistic number, my question is how accurate are these estimators? It seems there are so many factors that may sway that number (based on exact location/amenities) that it is hard to get an accurate estimate to analyze the deals.

I have done my research and feel confident the properties will still cash flow with Long Term Rental rates in the area, but will cash flow a much higher rate if the STR rates on the estimators are accurate.

Has anyone found a better way to analyze a deal for STR?

Any suggestions to maximize the monthly income on new STR's would be appreciated!

Thank you all!

I'm thrilled to begin my journey into buying short-term rental properties. The idea of owning and managing vacation homes that provide memorable stays for travelers excites me. It's a unique opportunity to combine my passion for real estate with hospitality, and I'm eager to dive into the process, build a portfolio, and create welcoming spaces that generate both income and experiences.

Hello! My name is Christine Myhre; I'm a wife, mother, daughter, sister and grandmother. I have owned my own Cottage Food business and have spent most of my working years in the food service industry.  I am very new to investing in real estate. I took a complete career change about 6 months ago and am now an Administrative Assistant for a Commercial Real Estate Appraisal company.  I have always been interested in Real Estate and being the appraisal environment, has made me even more interested in it. I am looking for a way to make an income that would allow my husband and I to retire from the 9 - 5 world and enable us to have some time to travel.

I look forward to learning as much as I can so I can make wise investments. 

So I've found a regional vacation market, the Poconos, that seems like it has properties in my price and potentially sufficient cash-on-cash returns to be worthwhile. It's not the only market I'm looking at right now, but I'm trying to avoid getting caught in analysis paralysis and keep moving forward.

I've been connected with an agent there who is apparently working with a few other STR investors and does good volume relatively to other agents there. Apparently, she hasn't closed any STR deals for buyers yet tho and didn't mention owning anything herself.

Now that I've found a market I'm interested in, what are the best next steps for me?

- Should I just start getting into the nitty gritty analysis using airdna of each property that this agent sends me?

- Should I try to keep looking for a different agent who has more experience with STRs specifically? Do really good STR agents help you do the analysis or only bring you deals that already have good cash on cash returns?

- Should I use tools like airdna and mashvisor to try to surface properties with good cash-on-cash potential according to their algorithms, and then bring those deals to her to compare them to her on-the-ground expertise?

- Something else?

How would you proceed? All suggestions are welcome! (Also any connections you have in the poconos or thoughts on the market there would be very welcome!)

I'm a new host who started hosting about two months ago, and I recently listed my property on both Airbnb and VRBO, approximately a month ago. During this time, I've had 1 booking on VRBO and 3 on Airbnb. The VRBO guest left a 5-star rating, and on Airbnb, I have one 5-star rating with another on the way.

However, I've noticed something that has raised some concerns, and I'm not sure if it's specific to VRBO or related to my listing. While I'm aware that Airbnb tends to boost new listings, I'm uncertain about how VRBO works in this regard. Here's the issue: Airbnb is showing 14.3k search impressions between December 13th and today, whereas VRBO only shows 232 in the last 30 days.

Is this level of search visibility normal, even for new listings, on VRBO, or could there be something potentially wrong with my listing on the platform?

I am trying to look at some priorities comps and referring airdna and rabbu and noticing significant differences for a couple of same properties. Based on your experience whose data you feel more realistic? 

Hi all,

I am planning to purchase my first STR in Fort Myers, FL sometime in 2024 with my brother. I have two other properties in my home state (NJ) with long term tenants, however I plan to sell one rental and 1031 into this STR, as I feel there is more money to be made in STR in a nicer area like Fort Myers?

I am looking for anyone's thoughts/opinion on that statement about STR > long term, as well as any pointers to begin looking in this specific market , checking out comps, figuring out if certain properties allow STR, etc.

I just found out about AirDNA which shows the analytics. Any other websites similar to this, and is it worth upgrading to basic plan?

Really any pointers about any of this would be helpful. Thanks in advance.

Hey All! Looking to purchase a short term rental (airbnb) in Florida and am curious how I would protect myself against potential lawsuits in the unfortunate event of an accident on the property? Is there STR insurance products for this ? Should I look into an LLC? Many thanks in advance!!

My wife and I have been talking about purchasing a STR somewhere in the Florida Panhandle. Prefer single family home to condo but can be swayed depending on thoughts here. My question is this? Is it possible to cash flow a STR and my family can use it for a week or 2 per year? I know if we use it during the busiest time of year that will cut into our profit but we are thinking of buying a few STR in the next few years in destinations we like to visit.

This will allow us to have a vacation home that someone else pays for but build us equity as well. If the market appreciated, then we will have even more upside. I know STR is a lot of work potentially and people don't take care of a STR like they do their own home, but this is very appealing to me to park $75-100k as a down payment for a vacation home such as this and use it as a STR.

I know there are lots of threads on this, thank you in advance. Any other markets we could cash flow a STR and use it a weekend or week per year. I was researching and national park areas seem to be popular but I also don't want to be in ridiculously competitive markets either since we are newbies. Thank you in advance!