@Elbert Dockery the landscape is definitely changing for sure.

With that, we made sure they paid for all related expenses....the cost to run new line, the repairs to our yard/ new landscaping, our attorney fees, and an extra fee for an easement.... and a deadline for said work to be completed. 

@Bob Floss II, do you know much about the AirBnb rules for renting out a single room of a unit or a garden unit in Chicago?

I have reached a "critical mass", making it difficult for me to continue to scale without delegating work out.I began by hiring out lawn care/snow removal a few years ago, and found a great reliable guy who, sadly, closed his side hustle landscaping business a year ago.  

Then freshened up the outside with painted shutters and a little landscaping.

The neighbors were so happy I fixed up the place, they used to bring me stuff from their gardens when I was over there working.

I have a little bit of capital, I work for California Pools and Landscape as a desinger/sales and I am a licensed real estate agent with HomeSmart.

I would like to have them pay for gardening, pool maintenance, and plumbing.

I usually check Craig's list to see if there are any off-mls deals at a bargain.Maybe take it off the market for a month, do some minor work that gives it a more updated look (paint, landscaping etc) and put it back in the market at a competitive price.

Should landscapers for my rental properties be insured?