From there you could work out a payout for bird-dogging for them.

I had to work out a deal with the bank to allow me to make only $650/month mortgage payments for the first 2 years so that the property could just barely take care of itself.

If he wants all his cash at once you could buy the house from him using an FHA loan once you qualify for the loan.It sounds like if this one does not work out you will be in a position come September to qualify for a loan yourself and not have to go a more difficult route.

Looks like classic BRRRR should work out.

There is such an enormous amount of work out there that they can pick and choose what they want to do that day and they're doing it based on what pays the most quite literally today.

With the higher mortgage it now becomes a higher risk if I don't have it fully rented, where as right now I only need 2 renters and the numbers work out great.

There's plenty of work out there, and you can learn while making money. 

You may work out a deal with an experienced investor who'd buy it, will pay you a finder's fee and you'd be shadowing the whole process to learn how to do it right.If you do have experience:1. 

And if the deal is right, it could work out numbers-wise as well!

Will see what the city says about it and will let you know if the numbers work out.