I have a rental property in Dennis and the roof needs replacing before next season.

Hey all. I have a rental property in Dennis and the roof needs replacing before next season. The complication is that the place is booked through the summer, so the work has to happen in a fairly narrow window in the fall, and I live off Cape so I cannot be there to supervise. I need somebody reliable enough to work without me standing over them. How do people handle this from a distance, and what should I put in writing beforehand? It is a three bedroom cottage, asphalt shingle, nothing architecturally complicated about it.

Put the schedule in writing with a start and finish date, and agree on daily photos, because that is what replaces you being there. Any decent outfit will do that without being asked twice. Also agree who handles debris and where the dumpster goes, since a rental neighborhood will complain fast. We used roofing contractors in Dennis, MA on a place we do not live near and the photo updates made the whole thing manageable from a distance. Book the fall window now rather than in August. Everyone with a rental on the Cape has the same idea about the shoulder season. Confirm the dumpster placement in writing too.