As for the 2/1 unit There is a long term tenant (10+ years) that has a great relationship with the landlord (they seem to be friends as well) and has been paying rent on time ever since they have been there.

But they won't do 75% LTV or it'd be a slam dunk.With lender #1, I'm paying higher fees of $5862 to cash out 5% more ($22,500), so I only get to keep $16,638 of it.

You'll likely have to pay cash for the property as it's unlikely you'll find financing for this type of endeavor. 

which means that if you're making the minimum payment, you're not paying down the principal AT ALL. 

I am in georgia.Hey there,First off, congrats on paying off all your debts—that’s a huge achievement!

I’m less concerned about the small items, and I focus on where big costs surprises can come up (new sewer lines, breaker upgrades, galvanized piping, etc) so I can re-trade my offer appropriately.

Unless new companies move in and create replacement jobs, only low-paying service sector jobs will remain.

Also avoids a pre-pay which by the way when does yours end? 

Couldn't pay me to have an STR there though.

What other factors should I pay close attention to in either the deal or when reviewing the physical property?