I restart all the time feeling the same as you.... "i should have done this or that from the start...".
After having spent too much time thinking about why i do this ? i've realized it has nothing to do with the game and all with me, with how i am...
I'm not the kind of person that will wonder around without a goal for a long time without getting bored. Because this is such an open game i need to find my own "guide"... so i'm always trying to get to this "perfect" start, this "perfect" set of self-imposed rules that will guide me and make my game better... But there isn't a perfect start in the sims, just as there isn't a perfect way of playing it.