How do you structure your team? Handyman vs Specialists

[Tone Church]

I have been renting for a year. I have two rental properties. So far whenever there have been issues I couldn't handle I have called specialists (electricians, HVAC technicians, etc.) Someone suggested I get a handyman and lately I have been thinking that despite having a few contractors I have relationships with that have done quality work I don't really have a "team" or collection of people to call on that I trust for fair pricing and good work and reliability. It works for now but if I'm going to scale from 4 units to 40 units I need something a little more structured and thoughtful so I can feel confident.

My questions are:

1. how have you structured your team?

2. What was the process by which you built it?

3. In what situations do you rely on a handyman instead of a specialist and what is the difference in terms of pricing (I'm sure it varies by area and I am in the Hudson Valley of NY)?

4. What other considerations should there be? I understand they should be insured and licensed when required but what else?