My initial plan had been to do something like Rent-to-Retirement or REI Nation- assuming that I'd be leaving money on the table to pay for their expertise, but hoping that I would learn through the process and develop the confidence to strike out on my own later. 

You can assume about 1% in closing costs in addition to commissions so you're starting around 7% before the seller gets any cash at closing. 

Selling the investments, paying the capital gains tax, and paying off the mortgage would save you $91,356 over 30 years.But...The total appreciation of $172,500, assuming an average stock market return of 7% annually over 30 years, would be approximately $1,313,114.  

However, you could assume a VA loan and get secondary financing and only put down 10% of the purchase price and get a low interest rate.

If you're in a position to contribute the 401k max, plus HSA max, plus even more I would assume you're in the 22% tax bracket or higher.  

I am assuming that it is vacant so showing it should not be a problem for you.

Assuming you don't plan on going back into any consumer debt again I like your plan versus barely getting by.

It's not clear in your post how heavy of a lift these entitlements are but assuming value is being created before a shovel enters the ground the initial LP investors will want to be compensated and share in the upside that's been created.

If I’m setting up leases I assume I need this license.

Assuming I purchased a property, how do I find renters?