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 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.

Lenders have liability in baiting borrowers, with disclosures, rejecting loans, in giving loans, or collection and servicing requirements, liability concerns are huge compared to real estate, violations carry ten years in prison and/or $100,000.00 fines, you better know what you are doing, and there are many brokers out there running small shops that have little if any compliance awareness.

As far as the garage concern, it was not included in the lease. 

Is that dangerous?

If high rates are your primary concern, you could potentially look around for a similar arrangement.

Even if OP can complete a purchase in Cleveland with $23K, aside from valid concerns others noted about reserves, is the risky asset in a distant market really the best place to invest?