Figure out what the root of your problem is and get to work fixing that.

So I guess you could say that I am hoping to move back to my roots for a little bit of both work and play. 

BRAVO Ashley for understand and keeping the family first :)  Any JV or partnership can easily be dissolved, but don't let REI come between you.I have trouble with both 1&2 as they are both rooted in lack of RE education. 

The roots can be deceivingly deep. 

@Davon Lowery this is very interesting problem, but you haven't shared the root of it; what is it EXACTLY that made this couple give up?

Compared to OKC, it will be a bit of a shellshock.I recommend sticking to your roots in Oklahoma and eschewing investing in Bay Area for now, unless you are willing to swing around some serious capital on flipping.

It's been around 3 months since I planted roots here in the mile high city and it seems there is some wind in the proverbial sails. 

Your future in Milwaukee sounds uncertain, whereas you will always have your KC roots, so I would go with that.Very generally speaking the cities are similar in the affordability and cash flow potential of rental properties.I have to call you on saying that Milwaukee has worse crime and shootings.  

My question is; how should I keep from accidentally putting down roots or making too many improvements.

I enjoy the challenge of providing myself and my investors double digit returns year after year while giving them the confidence rooted in the fact that every investment is based in a deal based on value.