Less is more with regard to having maintenance of shrubs and landscaping.

Repair foundation, updated siding to front of the house, used medium to high end finishes, beautified the landscaping What was the outcome?

Trim your trees and landscaping. 

-Long term holdMy rolodex isn't that great for trades (Plumber, Electrician, Roofer, Landscape, or Property Manager).

Upkeep and maintenance, landscaping, garden and fencing in the backyard.

They'll go away.If this were a $2,000 rental and you held it for two months, that's a loss of $4,000 (actually more because of utilities and landscaping).

I'm looking for suggestions on contractors to work with especially the landscaper,  pool rehab and cleaners for maintenance  Thank you for your help.   

The cost of land generally includes the cost of clearing, grading, planting, and landscaping.Land preparation costs, such as landscaping are depreciable Certain improvements made directly to land or added to it (such as shrubbery, fences, roads, sidewalks, and bridges) are generally depreciated over 15 yearsKeep in mind that depreciable rental property costs with a useful life of 20 year or less may be eligible for bonus depreciation.I don’t think the sources that you found are accurate since some of the improvements you mentioned can be depreciated and over a shorter period of time.

Hopefully it's out from under the foundation and beyond any porch or landscaping outside the building - and it isn't under a driveway.Next hire someone to repair just that section.

It's part of the landscape of the W 2 wage slave.