I thought the whole exchange was odd since I told him from the beginning I wasn't even looking for funding at this time but he definitely wasn't legitimate. 

Their standards are higher than any normal renter which is odd based on the type of clients they represent.

Typically they have been restricted to Wall Street type products like stocks, bonds, and mutual funds.

However, if rent control is too restrictive, it will chase housing providers out of the city.

The current area we are living in is very expensive (Boerne, TX) and is a heavily deed restricted region.

This will improve your odds of successful flips.When a wholesaler has a bunch of flip buyers coming to the house at the same time or throughout different times, your odds of getting that deal at a number that makes sense diminish.

They have restrictions in place that place limits on days per year, occupancy, etc- but it's still doable (& profitable). 

What a great town.Check out - https://www.cityhs.net/1265/Short-term-Rental-InformationShould have some rules and regs for you to peruse.I will say that lakefront is often restricted or banned for STRs there.

My main concern is that someone  told me that there are HOAs whose rules are so restrictive that people who bought lots found they couldn't even build.

My approval odds aren't great, I'm a first time investor without any exciting financial history. 640 credit.