Several contractors refuse to work in Center Point because the city is awful at approving permits/requiring even the most basic tasks require a permit.

They love their Home but feel they cannot keep up with the caretaking tasks.  

Please go there, read about the comments from your fellow cultists or anti-cultists as you so desire.  

Is there a way to tell if/when you're working towards the wrong goals, or the task at hand just doesn't suit you?

And those that go out of their way the most (working extra hours, taking on extra tasks, etc) get rewarded the most.I'll do anything from hand them extra cash to give them a Home Depot gift card to give them a gift certificate to a nice restaurant.

It also forces us to think outside the box and delegate as many tasks as possible since we cannot be present to solve them in person.

@Chris MasonDon't be so hard on the humble old napkin....if napkins could talk, they would probably tell stories of multi million dollar deals that were put together on them.Besides, there is no app that you can calculate deals on that can also multi-task to wipe the barbecue sauce off of your mouth :)

They do often thankless, repetitive, and sometimes dangerous tasks in exchange for their "40 years and out" plans. 

I know one person who only ever works on specific tasks from their desk.

I'd do long-term unfurnished unless you can just leave your furnishings in there so its not a heavy task.