Paying a proficient short sale negotiator is worth it's weight in gold to increase the chances of a short sale being completed efficiently and in keeping a strong line of communication with all parties.

this is definitely something I will work on and improve for my next approach.

Yard work is fine, though I’m certainly no pro with it.Is this just a matter of speed and efficiency at some point?

No car.. don't bother.. unless you become a commercial agent that works in a certain sector with a large firm in a large urban area where you can manage walking or taking efficient public transit.. 

A 20% decline is good for this market, and improve affordability slightly.Next spring, who knows.

You get out from under the property, at a profit, they get a property that they can put sweat equity in, and still get a bargain that they can continue to improve even after. 

Your improvement could very well fuel other interest and raw land is generally cheap and easy to hold if not in a highly taxed municipality. 

Your CPA and attorney together can advise on best entity type for optimal tax efficiency.

I'm obviously not set on a 4plex as that's more of the most ideal/efficient situation possible. 

They seem relatively easy to maintain, very efficient, and here in Alaska, I feel like a lot of people try to minimize their footprint and expenses so they can buy more toys.