You should be able to see if windows, kitchen, baths, landscaping, etc are in need of upgrades or not.

They will be your linchpin for all of the rest of your relationships in that market (Contractor, PM, Landscaper).

If this Tenant's dog is destroying the landscaping, are you charging her for the damages?

Augustin Landscaping. 

I know on the west coast this would have zero chance without major modifications and landscaping etc. 

There are already hundreds of existing motor home parks as well as "resorts" with amenities like swimming pools, gyms and landscaping with sewerage and fresh water supply that conforms with the local zoning laws.

I.e. the tree is gone, so you won't incur that cost again, but if you or your tenants are not keeping up the property, you will have fairly large landscaping clean up bills every several years.And as others noted, you need to build in items in your reserves.  

It spans across 10 acres and boasts roughly 4 acres of mature vineyards, a single-family residence, parking lot, pool, wine tasting room and cellar, multiple smaller structures (barn, storage, garage), and beautiful landscaping.

Instead of having a single expense labeled “repairs & maintenance,” itemize each expense such as landscaping, lock changes, and drain cleaning.

Other than handy man look for a cleaner, plumber, landscaper, painter, roofer, and etc... before you move as it will be easier to line those up now vs later.