Players do restart, often to get a better layout, and from the posts I've seen they don't regret doing so. (a few do)
So you do need to think carefully before you take such a step.
I don't see why you shouldn't keep hold of the unorderables & achievements you have made up to now, as TC knows, you need to get someone you trust to hold your items.
Your money you can get via the other towns ABD, tho you do have to withdraw it and drop it on the ground in that other town, before you delete your town. Items you have to carry over individually to the other town.
If you like your town layout, where your main buildings are, the features you have etc then keep the town you have.
If you are not happy with the layout, then look at the town features guide on animal crossing community, & the town map repository to get an idea of what you can get.
Grass design, town gates - there are pictures on the wiki. Theres also a few pictures of different villager house styles on there.
There was a good thread on villager house styles on animal crossing community but it wasn't stickied and now dropped off - it may at some point come back as a sticky.
http://www.animalcrossingcommunity.com/Topic/4823198/1/Town_Layout_Guide
(may not work as I cut the link short, but its easy to find).
town map repository
http://acfun.wallypogsbog.com/townmaps.htm
I restarted several times when I first got the game, to get a layout that worked for me.
I wanted all the main buildings close together, tho that has meant, keeping the grass in that area, has been a losing battle.
I wouldn't restart now, as I've put so much effort into the town.
My layout is a compromise, I didn't get everything I would have liked, but enough to keep me happy.
