There is almost zero chance that you bring this issue to a head and they sign a lease with a good future prospect for the tenancy.

For me, start with either the property who's lease expiry is furthest out in the future OR property that has seems like it will be easiest to manage.3) From what I have heard, rent has really moved upward in GVSC - I'd call a couple RE Agents or property managers that have rental listings in the area and tell them your situation / ask them to send you closed rental comps.

We contacted several hundred banks in one day and continue to follow up with them regularly....numerous lists came in along with future lists coming to us as well. here is a short video on that first day of bank calling.  

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 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.  

Hey Jacob,Congrats on building equity in both properties—it sounds like you're in a great position to leverage your assets for future investments!

If you have your current needs covered and are investing for the long future, i.e. retirement - then Roth IRA is absolutely the way to go.

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.

If you are looking to expand to other properties in the future, that option of a cash-out refinance or HELOC on your appreciating asset is always there. 

I think a 1031 exchange wouldn't be a bad idea if you're not making much on the property, and are worried about big repairs coming up in the near future.