They don't always account for differences in finishes, location nuances, or other unique property features.

- Which features or tools would make your day-to-day tasks more manageable and efficient or save (or make) you more money in the long run?

Our system is a bit unique.

They have been buying Greek junk bonds lately along with all kinds of other oddball and unique investments.

All that aside I'd do it, especially the part about including your kid and exposing them to the experience and related tasks.

Each of these have their own attractions and draws and unique activities. 

Do you need unique checks and balances in your away market so someone is representing your interests in the away market--yes.Slow and steady wins the race.  

And the simple task of directing the money to be sent to a second title company would constitute you having constructive receipt of the funds. 

Now, we do live in a small town, touristy area that does lack in nicer/unique short-term rentals. 

If you're up to the task, listing on Zillow or Redfin will be your best bet.There are numerous studies that show listing on the MLS will not only get you more net proceeds but also eliminate the liability from you as the owner by using a third party to sell the property.