When I first got ACNL, I didn't consider anything like "dreamies"; what I got was what I got, and I was pretty good about what I got, too, for the most part (I didn't know ANYTHING about villager resetting!)
minus Diva and Hippeux. Didn't know anything about The Bell Tree Forums and I didn't make communications with people on forums, so I was pretty much "on my own" (minus a couple IRL friends).
New Year's day came around, and I reset (cuz I wanted to

). I spent like 3 days or something resetting (wasn't really looking for a specific map, more of I was looking for oranges and decent villagers). I
did get this one town that I thought was cool (Town hall and ALL of the villager homes were crammed into ONE corner in the map), but I ended up letting it go very quickly because it just didn't work out. I eventually got this one map with pretty decent villagers and oranges as I wanted at the time, and I ended up getting a REALLY good map and I didn't even think about it. Still didn't think much of dreamies at the time until around the end of my time with that map, but I did miss a couple of my old villagers for awhile.
I have to say, I was FAR in development of Keydrake (second map). Heck, around the end, I got the
Emporium! But I decided I was running out of excitement, I was starting to get bored of it, so I ended up letting it go and starting new again. Surprisingly, I only took just a couple of hours or so to get the map I have this time. So here I am on round 3 (kinda), and I'm working on a list of dreamies. I already have some villagers in mind from my past experiences, (like Papi who was residing in Keydrake; I love him sooo much,) so we'll see about that.
I think of my villagers that I
miss, are Rodeo (first town) just a little, and Papi (previous town) a fair amount. I did have merengue and rudy, so I kinda miss them, too since they were cute, but idk if I'll be aiming to get them in my town. As for the starting over part, it depends on how rich you are. I emptied out just about all of my IGB for TBT here on the forums, so I technically "still have my money" in a way. If you want your IGB back in your new town, you shouldn't suffer too much, but because I'm
making all of my bells in-game (at least I plan it to be that way) rather than on the forums, I do have a bit of pain having to squeeze out whatever bells I can to finish a stinking bridge QUQ Oh well.
ANYWHO! Before I make this long enough to be tagged as an essay, I'll leave it with a form of summary: I
do miss a couple of my villagers, but 1 I'm not attached to and the other I plan to get in this town. I'm broke, so it's a bit hard, but I'm okay with it because I know that once I really start working on getting the bells I'll be able to pull through (also if I really couldn't I could get bells here on TBT). Town resetting can take awhile if you're really picky, but sometimes, (if you're lucky,) you can get something good fast.
Hope this post isn't TOO long for you

If you manage to read it all I tip my hat to you and give you a cookie.