I generally wish I didn't over analyse things, that's the path to making yourself super miserable even in very good situations. Equally I wish I didn't accept remarkably low standards from those I love. You'd think the two would balance themselves out but they don't, but then perhaps that just the typical Catholic guilt and Jewish neurosis of my heritage :) x
I also wish I'd bought two pairs of my favourite Red or Dead boots , the first pair looking a bit sorry after 5 years of wear now, and they don't make the same ones any more :)