Talk with a local insurance agent.My biggest concern is that you'll have to dump more than $16k into the reno.

Getting a beautiful property rented out above 3000 per month is not your biggest obstacle..

So..that is probably the biggest reason we would love to go ahead and find House #2 (found 2 great possibilities) and move. 

Further, there's around 20 items on autopay, newspapers, cable, internet, phone, medical insurance, etc.

Biggest thing is anticipating problems before they happen so when they do (they will) you can have options.

This has been the biggest red flag with under market properties that you wonder ... well, why can they be had at a certain price, and everyone avoids them because of how costly and risky foundation fixes are.My question is, has anyone actually done a major foundation fix?

Difference between 5.75 and 5 is $27/mo so its not going to be your biggest expense by far

My biggest advice would be to not have your Sons mother put down much at all for an option deposit. 

This might require some extra work, but ultimately people feel more independent now with all the information out on the internet.

What do you think would be the biggest upsides to going with a home possible loan VS FHA when they are both low down loans?