Yeah, I've had a few move out that I was sad about and regretted. Katt was my starting sisterly villager, and while I didn't like the look of either her or Coach when I started the game, I grew very fond of them quickly. She was only around for a couple of months - she asked to leave in May and I said sure. Within a week I was super sad. Coach didn't leave until November, and at that point I was okay with him going. Sure, still kind of sad, but I didn't regret it. The only other one that I regretted was Melba. She was super cute and I only had her for like a month or so and then she left and I wished I didn't let her go so quickly.