I don’t think this is a terrible idea at all. It sounds like you’re reaching the point where the business needs clearer lanes.
If handyman work and contracting work have different job sizes, scheduling needs, estimating processes, and production timelines, splitting them into 2 crews can make a lot of sense.
The bigger risk is creating a “crew lead” role before the responsibilities are really defined.
If one guy is going to estimate, schedule, and run the handyman side, I’d get very clear on:
You’re already doing the right work by tightening up requests, jobs, job costing, and time tracking first. That gives the new structure something to run on instead of depending on everybody remembering how things are supposed to work.
I’d probably treat it as a trial period before making it permanent. Give him the handyman side for 60–90 days, watch capacity, gross margin, callbacks, scheduling, and how much of your time it actually gives back.
If those numbers improve, you’ve probably found the next layer of the business. If they don’t, you’ll know pretty quickly where the structure is breaking.
