@Faris Wright NACA is one of many down payment assistance programs that exist. 

One Point is 1% of the loan amount, so if your loan is 300K, then one point would be 3K.   

I want to occupy one of the units, my preference would be the 2/1 so I can collect more rent from the 3/2 to go towards my mortgage.

No one is skating on this one!!  

For example, the house is old so if they see all new PVC plumbing in it and there was not even one permit pulled for that, you can be sure it's an issue.Here in Hollywood, Florida....I know a guy that purchased a home. 

I was looking at one point to also rent to operators since I still have my W-2 to focus on.

A much needed one!

You now have $5k in unreimbursed expenses, and 2 houses; one with a $200k mortgage worth $250k (giving you $50k in equity), and; one with a paid off HELOC, value and mortgage unknown, but presumably with more than $165k in equity.You should also treat the $5k unreimbursed renovation cost as a debt and pay it back (even to yourself) accordingly.There is no tax due because not only did you not make any realized gain, but there was no sale. 

We do this type of analysis in Reno, but instead of going one property at a time, we do it for the entire market simultaneously, so our clients can see the best deals based on potential cash flow and compare them to others in the market. 

this is a hard one. background services like identingly.com might not pick up any history.