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.

My other concern is they are supposed to be building another round of these and they can't fill the ones on my street. 

@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.

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.

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.

If you’re concerned about paying personal capital gains tax, remember that flipping the property means you’ll take the profit all at once, while with BRRRR, you can defer some taxes and have the property generating income.So, here’s what I’d do in your shoes:If you can make a decent profit flipping and then use that cash to roll into your next investment, you might be better off taking the cash, at least for the first project.

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.  

If you are truly concerned with liability, these should be your main concerns and focus, not whether to create your LLC in Wyoming or elsewhere. 

I understand your concern it’s always important to ensure everything checks out.