Other than hitting the phones, marketing yourself properly, as well as mastering your trade, just deeply root yourself within a few groups and let people know what you do.

Turns out the tree next to the house has a root that's pushing into the basement wall, the foundation is going to need some repair which isn't too scary, but this isn't a good first investment for me.

Any of those 3 are going to stay under 25 feet in height and roots that are well behaved.  

Yes, they have roots that can get into cracked sewers and their leave can clog gutters.

You can do root canals on your own too, but it's awkward and causes a lot of pain.

https://www.fast company.com/90880031/AirBnB-launches-rooms-short-term-rental-laws

My roots are in Chicago, and it's hard to see anything changing in the reasonably near future.   

Based on my experience, I have found that engaging the services of a skilled and meticulous exterminator who emphasizes the importance of tenant preparation can be an effective solution to pest problems.It is worth noting that in instances where the extermination process has not yielded satisfactory results, the root cause is often linked to non-compliance by the tenant with the prescribed pest control protocols.

Lots of root intrusion and chunks missing

Root in Sewer Line: There is a root from a mature tree partially obstructing the sewer line next to the sidewalk.