I love it and use it, and it CAN be done indefinitely, but as scale increases other methods become more ideal

Ideally you want bank statements or at least deposit slips.

I’m closing on my ideal 4-plex near a major university and medical centers using an FHA loan.

The main thing with associations is you don't buy into one that is too broke, ideally your reviewing some financial data before offering, not always practical though.

Ideally, the solution will also be something economical    What would you do if you were in my shoes?   

They're ideal tenants, worked with me on some maintenance issues, paid on time, good credit score, quiet, everything.

I don't foresee myself buying a home in the immediate future, seeing as I'm currently broke and just graduated, but ideally I see myself buying and renting out multifamily properties. 

Ideally they're interested in a small turn key opportunity that would allow them to operate a short term rental business while also utilizing the space personally for vacation - great idea right?!

I think your application would not look favorable to most landlords that have decent places - ideally, we want tenants to stay a decent length of time.

Ideally the property will have one unit that is in livable conditions so I could get that rented out right after purchase and then update the other unit.