Of course, there is the little problem of the constant upheavals, that changed the landscape several times, usually while Morgoth was being defeated. Still, the area that would become the Shire/Bree region seems to have been fairly stable. It wasn't drowned like Beleriand or Numenor, and no new mountain ranges popped up in the middle of it. Maybe this was because of Bombadil. That's something I haven't thought about before. I wonder if part of the reason why Hobbits settled in the area was Bombadil's presence. I bet they'd like the same sort of land he would. In a way, they have a lot in common - a lot more than he would have with Dwarves, for instance.