I totally understand and acknowledge the idea of investing where you currently live. 

I have made some local connections for contractors to do something solo when my current projects wrap up. 

Find a partner, find co-workers/friends/relatives you wouldn’t mind living with, find a property you can buy for less than your current rent.

Simply gifting him half the property now wouldn’t immediately allow him to claim the exclusion without fulfilling this residency requirement, I don't believe.One thought would be to use a HELOC to pull just enough equity out of the current home and use it to buy a smaller home, or at least the down payment.

@Austin Green we currently live in Franklin (short term)!

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

Is this a 2 bedroom apartment that is currently being leased (in the eyes of the CHA) as a 1 bedroom apartment?

But to your point, a current project I’m about to start, I can tell you I had to push back on ARR as the comps used by lenders were entirely outside of what I’m bringing to market.

Attend your local REI meet-ups and try to find someone who is currently house-hacking or has house-hacked in the past to learn from their experience.

Major brands like Ritz Carlton and Waldorf Astoria are currently developing property there, where they have traditionally developed in Miami, Fort Laud, and Palm Beach.