so proposing that they could do that but then that he won't have signal when he gets there is ludicrous.
Depending on the work crew to have the same repeater that you need is what is ludicrous. Roughly a 1 in 3 chance - and that's assuming that they'd even be bothered... I've never been asked to hang a repeater and I suspect it is not a very common practice. He's not supplying his crews with phones and he's sure as hell not giving them all $300+ repeaters just to save $30/month on a phone bill. Payback period of 30 months or so is not very cost-effective.
Further, work crews working in areas without electricity use air or electrical tools powered by a portable generator.
They often use batteries now. If they do have a generator, there isn't exactly a ton of surplus sockets, it's on-and-off, and a terrible source for sensitive electronics.
(work crews have comm, but Bob doesn't have comm when he visits work crews).
I never said his crews had communications, and if they do it's because they have Verizon or are stepping outside to make calls. He needs to be continuously reachable, not them.
You also still haven't addressed how repeaters would solve his rural/industrial coverage problem when he's on the road or between sites.