@Truong Vu You have some valid concerns, but most investments, whether for your personal use or long term holding property is usually about leveraging what you have.

That’s good to hear about mid to higher end rentals as that was partly a concern of mine.

yeah that was exactly my concern too with regards properties sold around that 3 year time frame. i'll definitely reach out and let you know.

Kissimmee is still a strong STR market, especially with Disney nearby, but competition has increased.The smaller pool and backyard might be a concern for some guests, but the privacy from the freeway could be a nice bonus.

However, I have some concerns and would appreciate advice from anyone familiar with the market or STRs in general.My Key Concerns:Lack of Comps: When looking at AirDNA, there aren’t a ton of comps in the area for properties like the one I’m considering.

If prospects upload ID, pass a quick background check, and maybe upload a pre-approval letter, I think that answers both the security and tire-kicker concerns. 

Also, the owner expressed concerns over the capital gains tax early in the discussion...so I am thinking the opportunity to do vendor financing will help me get a good purchase price and help the vendor with taxes.  

I've personally done 60 deals in Detroit this year and I've seen monthly property taxes anywhere from $20/mo (extremely rare) to $350/month.

One of the concerns I have for my children, especially my oldest is that I think I want them to have success  more than they seem to act like they want success.

However, one of my biggest concerns when fixing homes is knowing when to use permits.