He could benefit from not worrying about unloading a property he doesn't want, gets all the money he's asking for (eventually), and I get the cash flow with minimal expense to get in the deal.With respect to offering my co-worker more, I'm only considering it if it appraises for more.  

I am in R4 zoning which specifically allows for STR's, but if some smart guy who doesn't like me downtown wants me shut down, they could do this to me, and it would eventually work.

The music will eventually stop if distributions have to be made.The best protections for this is having a good accountant looking over the books.  

So ideally if you eventually get rents to market value by increasing at $250 per month you'd be up to $5300 gross per month.  

My goals here is to learn and eventually help out as much as I can.

However, if your spouse is just a bit uneducated, you could start your journey alone, and he could eventually follow.The last option would be similar to my own.  

Then eventually building a portfolio of multi units like yourself. 

Then when servicer asks for financials over and over again from home owner and keeps making the process difficult eventually the seller mid process gives up emotionally and the short sale fails.With a short sale you have to figure out what kind of loan it is FHA,VA, conventional,etc.

If your tenant's monthly rent is only covering the mortgage and you aren't paying for property management and you aren't accounting for major repairs, you are eventually going to be in the red.

Eventually, I want to retire.Rentals are slower money.