This led me to starting a landscaping company because of the volume of work offered by commercial property managers. 

If each building belonged to a different owner, the only thing that they would have to collaborate on is, obviously, the courtyard (gardening, each side has it's own sprinkler system) , the intercom (about $120/month for the phone line), and the parking area (needs resurfacing).  

If your property is leased for more than market rent, I would see if the landscaping/mowing would negate the rent increase.  

A friend of mine had a landscaper randomly do work on their property while they were out of town without being hired.

While visiting the house, there are numerous items which need remediation including flooring, light fixtures, landscaping, some drywall work.

Fence is entirely within my property per a survey that I did.In 2023, I did some landscaping work and replaced the front part of the side fence (and paid 100% for the replacement).

For investors utilizing the STR strategy, what is your "gut feeling" for what the upcoming investment landscape will look like in 2025?

The most common benefits a landlord can get from an arbitrage agreement are: reduced vacancy expense, decreased maintenance costs (most arbitragers agree to fix any damage done by guests), increased rent (most pay a premium), reduced number of hours managing the property (aka it's more passive)Some less common benefits, but still worth mentioning: Using the property to host their own guests at a lower rate during the "vacation season", Revenue sharing, arbitrage managing landscaping, and other management tasks. 

Then it didn’t pass the city inspection because of landscaping debris and tree branches that fell in my yard, so I put in $5k more.After 6 months of vacancy, a new tenant moved in and immediately began complaining about everything.

If you need help navigating this landscape, happy to have a call.