very rare you are gonna find a sheriff or authorities to remove someone between thanksgiving and christmas.

So while cash is necessary to keep the property afloat, I invest more for the appreciation of the asset.  

It seems like each option could work depending on your long-term goals for those assets.

The yield of an asset is a reflection of the risk of the asset.

I do have folks that don't book because of that.That is a good thing as not understanding the distance to get places will create bad blood and cause those 2 and 3 star reviews which no one wants to see.Like @John Underwood, our place isn't cheap so we don't get the folks that destroy places.The bottom line is that you are renting out an expensive asset to strangers for 3-10 days or whatever.

If you have a lot of equity and little cash flow, you may be better off liquidating that asset and reinvesting elsewhere. 

Your understanding of NOI, deal negotiation, and long-term strategy are assets that make you stand out. 

Typically a new roof only makes sense to protect the asset.

(if this makes no sense to you, research the 80's)Yes, fundamentals apply like compounding returns, proper use of leverage, appreciating assets etc etc, but the specific's of the how-to's, the "plays" one runs, how you play the game, it's a different game than '19'. 

How do you continue  guaranteeing a rate of return or redemptions when the asset class is real estate which is not liquid?