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.

It would be immoral to tell them they can't use the garage any more because you aren't charging them enough rent.2.

In this case the current financials on the property aren't great(rents well below market value and the owners family living in several of the suites) so the lenders will likely not provide the funding based on poor NOI.  

You don't need to add the extra step of doing a cashout refi as you aren't keeping it and it costs a lot of money to cashout refinance.

It's because agents aren't understanding affordability is constrained.

It’s safer, and honestly you aren’t spending it, you’re moving it from one asset class to another.

Obviously, some of these businesses and investments are doing well so a successful business doesn't imply that the owners aren't shady, which was one of the points I made.

The section 8 voucher pays $1,550 per month to 3 bedroom properties according to the Cuyahoga Metropolitan Housing Authority.

Plus most retail buyers and sellers like having an expert on their team to ask questions and make sure they aren't making beginner mistakes on what is often the biggest financial transaction of their lives. 

Also how do folks feel about Real Estate buyers who aren't investing for maximum Cash-flow, but instead investing for long-term equity, appreciation, and eventual cash-flow?