I will be happy with at least $100 cashflow and avoid the mistake of moving and committing to an area that will be far from my job and actually increase my living expenses instead of reducing them. 

That may cost some money but it may be well worth it to avoid a misstep in the long run.

Please let's share it all so we can help someone out there avoid them or learn from your experience.For me, it's trusting and relying on contractors too much. 

There was a different search page in the past that had an option to view landlord tenant cases; that seems to be gone, and you get a redirect to the new search page that does not have that option.My main use of that search is to avoid problem renters, so it still seems to work for that.

A few resources:  1)  Trulia.com  Put in an address and get an overview of the neighborhood crime rate, avoid high crime areas.  2)  Rentometer.com Put in an address, bed bath count and it gives you projected rates.  

Tips or advice on what to avoid?

I could be wrong, but I think I can use the equity I've built up with this house to cover the 20% for the conventional mortgage and avoid PMI.

Avoid all real estate gurus selling their “systems”.

I want to make sure I understand the nuances correctly before making this suggestion to to my better half, so hopefully BP can give me good advice about this and make sure I'm thinking through the repercussions correctly.TL;DR My wife hates living in the South and wants out ASAP and our owned primary residence doesn't come anywhere remotely close to cashflow potential, so how do we leave before the 2 year mark while also avoiding a hefty inflation-induced capital gains tax bill?

Hopefully your device has a skip ahead 6-12 minute feature to avoid burn out.