@Max Emory Does it make sense to pay a bookkeeper to track your finances in Quickbooks over a shadow system (I use Stessa and a google drive for tracking my finances)? 

Property manager is also arranging a 2nd contractor opinion.As for new units, in my experience, I can get a new 3.5-ton split system either Goodman or Rheem from a source out of state for $2,200.  

Repaired the sprinkler system and revived the dying mature trees on the property.

You can make more money by working more hours, increasing sales, controlling expenses and opening additional locations in a good franchise system.

The property needs some minor systems upgrades and cosmetic upgrades that I pan to complete over a 9-12 month period while living in the property.

Blame somebody else so you don't have to be the bad guy when delivering bad news.I collect rent using an online system that automatically charges a late fee if rent is paid late. 

He planted some plants, installed a sprinkler system in the back yard and made the front and back look amazing. 

It forces you to work "on your business" instead of "in your business" because you aren't able to just drive by to fix something small, you're forced to develop systems to help you run things. 

Should I add ductwork and HVAC or add mini split “ductless” systems?

What technology/apps/systems have you used to decrease the amount of time spent on managing a similar properties?