For locating properties, it’s best to have someone keeping an eye out for you, especially if this isn’t your day job.

(i.e. there's still some risk, stress, etc. involved) Not to mention that paying 10% + leasing fees "goes up my bum sideways!

If the purchase price is less than the debt then you have a short sale situation which would involve asking the lender to postpone the sale so you can go through the short sale process. 

Once the tenancy ends the tenant should not be involved in the place in any way.

Make sure you check to see if they're involved in and organization like NARPM (National Association of Residential Property Management). 

I feel like the market is at the peak right now with prices increasing everyday, but I'm keeping an eye out and learning all that I can about real estate investing and house-hacking before I return.

So, he is going to keep an eye out, and he said if we need to get them out they would.

That just gave me tons of eye-opening ideas, thank you.

Wonder if you could negotiate before you get an attorney involved.

If his finances are not involved in the project, then he doesn't risk anything while you are risking your savings, so think about how you can decrease this risk.