In this instance this is a plan that can be executed upon and they have some control2.

I have done over 30k reservations and only had 1 instance of a guest causing above $10k in damage, so not sure how worth it is to pay for additional coverages. 

For instance, you could look into refinancing the property to access some of its equity while still maintaining ownership and cash flow.

Not sure how long you held the land, but there are some instances that the land can be used as a down payment. 

In instance above if you put in 42000 and get 1200 a year - 1200 / 42000 = 2.8% Cash on cash

Quote from @Jay Hinrichs: Bruce there is also that famous case in San Fran  in the Seacliff area of 5 to 30 mil homes and someone bought their right of way on a small private street and were trying to block them off and then of course sell it back to these folks.

The City of Portland, and Multnomah County are more restrictive than most of the state for instance. 

It normally doesn't cost you any money to open and to be able to access that large amount of equity to buy or stabalize your current portfolio allows you so much more opportunity costs.For instance, I took a $200K LOC out on my primary residence when I first started in real estate.

For instance, in places like Austin or Chicago, I’ve noticed similar deals pay off when you have the right property management systems dialed in.

For instance if I’m looking at potential capital expenditures over the next 5 years and the range of the cost is between $25k and $75k, I would use $75k in my projections.