When I restarted my town back in January, I set it back to the date I got the game initially (Christmas of 2014). I TT'd forward slowly, and now I play in real time (unless plot resetting)
I think I set mine back a week just because it had just changed to a new month and the previous month had some exclusive bugs that I didn't feel like waiting 11 months for.
no, i just started at whatever day it was. i think because i was so excited i had got the game, i forgot all about time travelling to a specific date completely
when i first got the game, i started on the actual day i received it. my DS was dead for about a year until i got a new one and when i re-started and got a new town i started in october to enjoy all the fall/winter holidays, but now i'm back to the current date.
I don't remember when I started my main town but I started my second copy on September 5th to see what would happen if you started on a holiday, basically you just have to wander around all day without getting any advice because town hall is closed.