This eviction altogether cost me $20,000 - legal fees, lost rent, and rehabbing.

Yes that’s why I want to hold onto it is obviously because of the rate. 

He told me he owned a few mobile home parks in town (they were large and had high lot fees) and this is what sparked my curiosity.

At any rate it is possible, but depending on your appraisal it could be a gamble

When you sell a property that has been depreciated, the IRS requires you to "recapture" the depreciation deductions, taxing that portion of the gain at ordinary income tax rates.

Quote from @Pat Aboukhaled: Curious.. do you think a flat rate for the whole season feels more convenient, or would you rather pay per snowfall to avoid paying for a mild winter?

I talk to so many people who regret not getting a PM up front because they are having problems or high eviction rates doing it alone.

Rental rate?

Gaining a risk-free property, with a long-term resident there to pay down your fees, etc, with a property management company in place to hold your hand along the way and making sure your property is kept up with. 

It almost feels like they make it difficult on purpose so they get extra revenue on late fees.