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?

Looking to update our systems, looking for suggestions on CRM programs.

How many of you actively pay for preventative maintenance for the HVAC system and or other appliances (washer/dryer/etc)?

The previous owner was a master electrician and had upgraded all electrical systems and the property over the years-the clearly had a pride of ownership.

The previous owner was a master electrician and had upgraded all electrical systems and the property over the years-the clearly had a pride of ownership.