The tricky part is knowing when 2500 cycles has elapsed. I know LiftMaster has some things now with their enhanced MyQ that can let the owner of the unit know how many cycles a door has and I think they can share that information with their favorite dealer but you would probably want to check with your LiftMaster rep or other Operator Manufacturer on their offerings as more and more smart devices come into our industry. As for memberships (or even recurring services without memberships) that can be easily setup in Service Titan if you have a regular cadence you go out to these customers. For example, if 2500 cycles normally takes them 2 months, you could setup a recurring service every 2 months for a Preventative Maintenance job. You can add a membership to this if desired to have autobilling and some other features but you can also have recurring services without a membership.
If you truly want to service it every 2500 cycles and the amount of time between 2500 cycles varies greatly, you could always setup a task management item to call you customer and see where they are at so you dont lose sight of these jobs. Say it is sometimes 2 months and othertimes 5 months, you will use that task as a reminder to check in and see where they are at with the cycles on their door. Hope that helps.