My active work in the real estate is now focused around coaching others, investing in other peoples deals, doing a little private lending, and optimizing my remaining STR

Yesterday would certainly have been the optimal time to invest.

Is it eligible for tax optimization strategies like 1031, Sec 121 exclusion (you referred to as $250k tax-free profit)More details are needed to determine the tax impact of the sale. - Did you ever rent this property that you're selling? 

Where’s the optimization of productivity in that system?

You can find calculators for this using YOUR income / expenses by searching "Equity Optimization" or "Equity Advantage" input YOUR numbers and get a result.

I had to spend extra money to make repairs, replace tenants, raise rents, and get the property at a optimal condition before I saw my first positive cash-flow.

Anyone else find more pessimism than optimism out there?

If you can finance using private lenders (friends, family, business contacts, co-workers, friends of friends, other contacts) on 10 year notes at 7-8% (20-30 year amort), then that would be optimal.

Get a good web service like investor carrot and either hire someone to optimize it or learn it yourself lile I did. 

One of the three partners lives in Detroit - he's agreed to be the property manager and live in one of the properties if that's optimal.