I deal with this without charging the tenant if its not excessive. 

Understanding your top priorities can help in determining whether Stessa, Baselane, or another tool might best fit your needs.If you're comfortable with apartments.co for rent collection but want higher yields on your cash (this is me reading between the lines) you could have the transfers go into a high yield business account like BlueVine 1.5% interest or something like CapitalOne 3.9%.

He also doesn't control regulations in the states/cities, but his attempts to cut regulations may trickle down and impact personal property rights and people's ability to use their properties as they see fit.

Ideally one side would sell out to the other, as divorce is often acrimonious or can become such.

It's a great strategy but I agree with @Jack Seiden, having roommates at 30 isn't ideal.

I would say suburbs would be ideal for you.

Some of my clients in this scenario literally just pick-up the phone, tell the seller of their specific property they are interested and they are well qualified, and see if there is some kind of fit. 

I'd like the building to be within 10 minutes walking distance from a Brown Line L stop, ideally in Lake View, North Center, or Ravenswood.

Take it FWIW.I will say my recommendation is to not use the agents that fit the criteria of my first & second points.

In your ideal world who pays the buyers agent in that first time home buyers niche in Minneapolis?