I would regret not being able to finish my gen 1 pokedex. That was the goal from the start and being so close, it would be frustrating to quit now.
I like a lot about my collection and would feel decently satisfied about many of my achievements. I'd wish I'd gotten the golden ace trainer when it was still possible and the golden fisherman when it was still easier.
EDIT: I'd also miss having a reason to walk. I'd start playing Ingress more but it isn't as engaging to me and doesn't reward random wandering at all like POGO does.