Here’s what I’m wondering:-Is this a mountain town issue (snow-dependent shoulder seasons, regional taxes, etc.)?

I get it that you got some big chip on your shoulder, but that doesn't make stupid ideas smart ones. 

Solid summer STR demand with some shoulder season demand.

Standing on the shoulders of giants, so to speak.

Each size has a different width due to how hard it isto park a longer unit at the very front angle of their turn in. 20’s- 10 wide; 30’s- 12 wide; 40’s- 15 wide.

Old school, but it still works for new Airbnbs and STRs going live here in Colorado during shoulder season between skiing and hiking. 

You came within a hairs width from it all......

What I need is a successful mentor to look over my shoulder.

If we did split it four ways it would be over an acre per slice and it does seem to meet all the requirements (such as minimum lot width and road frontage etc.) for its current zoning as a four parcel set up.  

Trying to shoehorn a 1031 exchange into the mix sounds tempting, but it locks up every dollar of equity, keeps the consumer debt on your shoulders, and forces you to find a new property on a tight clock—hardly ideal when you’re already stretched.As for the “live there two years and skip the tax” idea, forget it; that break only applies to primary residences, and even then you’d still owe back the small amount of depreciation you’ve taken.