I realize your example that no one has the itch for garbage truck fleet management software, but I found myself (via my wife) in that exact situation about 3.5 years ago. She had founded a company providing food waste collection with composting on the backend and it became apparent very quickly in the market-testing phase that the challenges were rooted in logistics for consumer pickup and less in converting customers or processing (at least for our area in New Hampshire).

After a couple weeks of her manually designing pickup routes for the "fleet" I hacked together a demo using TIGER data and OR-tools that planned routes (with autogen'd tick-sheets) and calculated a rudimentary cost-per-mile. While it wasn't saving game-changing amounts of time over her initial route optimizations, removing the manual overhead of generating routes on a daily basis was a big win.

I would say it became a "fleet management" project (if you can call 2 cars, a trailer, and the occasional rental to pick up the slack a fleet) after one of the drivers suddenly heard a "grinding" sound while on route 5 miles from the nearest gas station. Based on the description I guessed that the transmission was dying and had them check the fluid. It didn't register on the dip stick so she dispatched another vehicle to tow back the trailer while the other one limped to the shop. The offending vehicle was one of the fraudulent VW TDI's that just had to get to the dealer's lot for the trade-in value (our goal had been to _barely_ get there under it's own power and it seemed we went a bit too far :) ). "Too far" was using it to tow ~1200# of compost 4 days a week for 6 months with what we determined to be one oil change at the beginning of that period. This experience led to adding a step to the route planning calendar events for maintenance checks for the vehicles in the "fleet" based on their current and expected mileage.

There were a bunch of things that I (in my night-time, engineering resource capacity) wanted to add to the system (tracking with GPS built into car, RFID readers in car and on bucket/totes to remove driver's manual annotations, CANbus diagnostic readout to identify early issues) but before any of those got off the ground she sold the company (hooray!) when we found out she was pregnant with twins and she realized she was way more interested in the physical composting work than the cost-center minimization of the drivers and the fleet anyway.