I might be able to partner on it to reduce my exposure as it would be a significant amount of my unused savings - meaning, savings minus my emergency fund and many other investments. 

Still did ok, but could have done better and the stress was not worth it.  

If you’re only looking to reduce your cost of living, then this deal might be worth it.

There are to many mechanisms in place to reduce the crash.  

The cash flow is what I trying to concentrate on but I would like to pull equity from my properties to reduce/eliminate my out of pocket.

Reduced fees and increased simplicity are always nice so both are at the top of mind, along with simpler operational overhead.

I would give him the $100k then as his time is money as well, HOWEVER, for that amount I would expect him to sign some kind of covenant that reduces his equity at certain tiers if he does not complete the project within a certain time frame or hit certain agreed upon milestones.  

This might reduce your $2300/month payment, providing you less stress and, hopefully, a little more left over with which to pay down your car and student debt.I also agree with the previous poster who pointed out that rent in your area won't be much cheaper than the cost of ownership.

Again, I would stress that judicial sales (and by extension repository sales) can divest the other liens.

You will also get tax advantages to help reduce your tax burden on your W-2 job.