My long term tenant (a family friend) is moving out and I am concerned how to make sure I pre-screen future tenants effectively without violating any laws. background: this property used to be my primary home and had a very informal agreement with a family friend to rent from me in the mean time.

No one will accept an offer like that (for future costs being too high) and if they do, there is an issue.

I understand the cash flow and cash on cash return will be lower, but we are looking at holding these properties for the foreseeable future so, we are expecting to make up for this with appreciation.  

This allows the investor to benefit from future buying opportunities in the REIT without triggering any capital gains or depreciation recapture tax events.

After that, all rental losses are blocked and pushed into future years.

I'm married, have three kids, and I live in an upper-middle class type suburb with the lawn and the white picket fence and it costs so much these days to keep a family there, it makes me worry about the future for my kids. 

I think what you're doing with your plan for your future is very smart and hope to contribute to your goals.

. #5 hits the most for me, as I’ve had and have many clients that either exit as a refi or a sale, but don’t consider the future value/costs based on that true future value or completion timelines.

They don't cash flow....at all, but the future benefit here is the option to build new once the neighborhoods continue to appreciate and get new developments.

Neither one of you are going to want to have to explain to your future spouses or significant others that you still own a house with your exes (and deal with that drama).