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. 

Leaky faucets, faded exterior paint, poor landscaping.

Just maybe landscaping, paint, new flooring, etc.  

Secure your landscape and pest control providers.4.   

We landscaped and never touched the pool and still made a tremendous profit.

Hi MeganBesides Mgt Fees and Leasing Commission, there are -- utilities (electric, water) and maybe the gas if your furnace is not working - rekeying your house (done at last)-house cleaning (done at last)-landscape cost (mow grass) -repairs -vacancy And much more.....

Maybe listing in order from greatest significance to least : flooring, new paint on outside, metal roof, central ac and heat in each unit, landscaping, updating restroom (shower, countertops), kitchen counter tops

so far just redid the flooring and landscaping. considering upgrading kitchen and bathrooms.