If, a year from now, you have an extra $20k piled up because you have been serious about this, it established a bit of a track record and proves that you are a doer and not just a dreamer.I would also express gratitude that you have a partner that is so cautious.

I ASSUME you’re talking $400+ in extra expenses for providing water, power, sewer, gas, internet, communal area cleaning, and exterior maintenance.

The extra 1050 a month definitely helped with the bank.

He is always having issues, confrontations, ongoing drama and the like.....You just provide an excellent service and smart people will pay extra.

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

I doubt if anyone is saying it's impossible for it to work but I feel it's difficult. I

Politely and clearly, make it extra clear that all information will be verified including income prior to the signing of any lease.  

They're pretty organized, but expect annual inspections and some extra paperwork. 

The quotes were only a few hundred dollars extra annually.

This is interesting and I look forward to the feedback.But, I don't know if I want extra buoyancy in a hot tub?