However, i am stuck with how to address landscaping.

Will it require exterior painting (repairs) or landscaping?

I am not sure about this company that has offered to do my landscaping and Financing (Strange combination!).

Tenants are responsible for their landscaping as well as utilities.  

Tenants won't inform you of these things unless they are an inconvenience (they aren't if the tenants aren't paying the bill).Low flow shower heads and faucets are also a good idea and will pay for themselves quickly.I would also close the valves leading to any exterior hose bibs and change out your landscaping to plants that don't need extra water.

On a side note these subs handle hard & landscaping and fences and decks so they really aren't ever going to be in the way of the subs that my PM manages.  

The current tenants have really destroyed the house and the landscaping, and it really needs work to get it back into good shape.

My favorites are landscaping and flooring. 

This building has high fees already at about $7/sqft but it includes nearly everything (electric, trash removal, HVAC, roofing repairs, landscaping, snow removal, etc).I apologize if some of these things seem like novice questions but I have scoured the internet without finding clear answers!

Some minor landscaping and repair the fence in the back yard.