While I doubt I'll be investing here (terrified that property taxes and the pension debt will ultimately cripple property values), I'm always interested in meeting new people.

I understand if you want to sell 1 of the lots, but I'm not sure about your concern about paying off the debt so that you own it free and clear. 

Now most of my deals are a combination of our business money, bank money, hard money, and private money.  

Eliminate debt, establish a budget, and save.

Would cash-flow very little.Obviously, a combination of the above is possible (pre-sell all but a few units, nullifying the profits, and therefore taxation).My feeling is that the first option would allow me to use profits to build something bigger (e.g., acquire another plot). 

Ultimately responsibly using leverage (both equity and debt), implementing systems and buying good assets with realizable equity  is how you scale while operating a sustainable real estate business.

I don't anticipate things to be that bad this time, but the value dropped over 25% back then and we are unsustainable at the point of the affordability cycle we are at now.You basically will be buying a monthly debt, speculating the value of the property is eventually going to go higher than you bought it for.

I have a duplex in cleveland with a combined 2,336 sq. ft.

A combination of these things?

If you are taking on debt for the STR this gets a little more complicated, but not much.