Sellers aren't always convinced by slick, polished "pitches", investors who claim to be there to "help" them, billboards telling them that the company buys ugly houses, or computer generated offers at 85% of market value.  

Good price too and the guy was honest no over inflated claims about lifetime warranties.

That I would later file a small claims for rent, late fees and any damages?

I would say that if you do this without the proper permits, you may have issues when you sell the property and try to claim it as one entire unit.  

There have been a lot of pan-handlers claiming it as prime real estate.For whatever reason, this guy set up camp today.Maybe it is because he was once a pan-handler at the same spot and things have turned around for him or he may just have a thing against pan-handlers.I did not ask him, why but I shouted out to him if he would allow me to take the photo and he said "sure".

Don't use any automated ways to determine values, that includes Zestimate, Redfin estimate, or any other tool to claim to values in an automated way.

I would check into your obligations as a landlord to tenants for your state to make sure that none of the claims hold any merit under this.

Can't claim to be successful yet as I'm just starting out and working a full time job like yourself but wish you the best of luck as you find your path!

I'd check on what the fair market rents were regardless of what the seller claims he was getting.

If you took pictures at your old GCs work, got several quotes from licensed companies, specified on that quote something like "remove non-compliant newly installed wiring" and have them done the work, then you probably have a bond claim up to $15,000, IF the GC is licensed and bonded -- which I don't see you mention.