If you find a newish development and become their "general services" supervisor or handyman, I've always thought that would work. I live in a development of roughly 300 homes, they're all pretty much the same. We all have the same issues. When one person's HVAC died, the houses all down the line went shortly after. Same with washers, etc. We share a listserv and share info that way, but if someone started a business to help me with home maintenance, I would pay for it. Think of it like an HMO, where you would be the primary care and do quarterly check-ins and then send the homeowner to a specialist. So in the fall, you'd send a message (or stop by) saying "it's time to check your gutters. Do you want me to check them and have someone come clean them?" And on a slow month you could say "I'm here to change the filter in your dishwasher".
Also: I'm here to check your dryer vent for lint
I'm here to winterize your hose bibs
I'm here to power wash your patio for the spring, inspect your sprinklers, check for water leaks.
I'm here to wash the filter for your microwave, etc.etc.etc.
The reason I say go for an entire development is because all the systems are the same and you don't have to learn too many different systems. Also, with homes close in vicinity, it save you time between homes and you can schedule service technicians for entire days for discounts. (That's what we do in my neighborhood...every spring someone arranges window washers and they call all interested homeowners with options for available appointments). So if one person kept up to date with all the things I should be doing to maintain my home, I'd pay for that service and on top of that, pay for any add-on services that needed a specialist.
