I might as well be the worst person to ask. I mention it a lot, but Punchy never leaves. If I can't get him to leave, I absolutely have no tips on getting anyone to move out. The biggest thing is to stay persistent, and don't let yourself rush even though someone is waiting on you. You can't decide who is going to move out next; the way I see it, they all have an equal chance of getting out. If the villager was the most recent move-in, you might have to move out another villager before they'll talk about moving, too. If they've been there a while, just talk to them. Ignoring them doesn't necessarily help, and neither does befriending them. Just talk to people, find out who's moving, then go onto the next day.
I've only just barely started my slow-cycling adventure, so I don't have many other tips than that (I can speed-cycle, and that's about it).
Thank you for the Lobo support!
I actually just posted him on Tumblr, so I'm gonna temporarily shut him off from the thread.
Seeing if I can get Freya. If he's not out withing 35minutes or so, I'm gonna open him back up or find a place for him (since I've got to let people in to weed, too).