@Andy Chen I'd recommend setting up a call to express your concerns and what you expect going forward.

First, let me express how it is such a blessing to have the BP Community to turn to for credible advice without.

I’ve seen examples that show how using leverage increases Cash on Cash ROI (expressed as a percentage), but you have $$ in your example.

He has expressed a desire to renew but is now over a month late in rent. 

Basically, you are just collecting unenforceable expressions of interest.  

First off I want to express my gratitude that such an incredible community exists.

Tenants should not make modifications or hire anyone to make modifications without express permission.

I intentionally looked to further relationships with people that expressed in some way a need or a deficiency in the exact area that I was strong.Offering someone free labor if they meet with you and figure out what you are good at and if they need it is probably not going to result in as much success.  

After the walk through they both expressed that I shouldn't buy this place and that it was a lot of work. 

Buildium has paynearme so you tenants can pay you at cvs, 7-11, ace cash express for $3.99.