So are you saying it may not be wise to refinance after the forced appreciation, or does it just depend on the interest rates?

Depends on the points value of your timeshare unit.  

Depends on the broker.

Takes an investment of $50k + depending on market.  

One hurdle you may have depending on location is zoning approval.

@William Coet, as noted, it sort of depends on where you are looking to protect liability.The most common reason I hear when working with investors who invest in a syndication through their LLC is honestly for ease of bookkeeping and record keeping.  

To answer your question the difficulty level of finding tenants will depend mostly on exact location and time of year.

I'm curious how many hosts update their listings depending on the season.

It all depends on numbers.

Ample parking space,plus reliable and dependable staffing makes a huge difference.