I have so many Sheps, they're from everywhere and have done everything!
Incidentally, I just this week finally got the last achievement on ME1. That is to say I got a Shep leveled all the way up to lv60! Took two playthroughs (well, one and a third really, didn't take as much grinding as I'd feared) but I must say, a fully levelled up Adept is hysterically overpowered. Also, by that point money becomes utterly meaningless. Seriously, I had top tier equipment for *everyone* (even Kaiden) and I was still maxed out on both creds and omnigel.
Next up, ME2 insanity playthrough with an Adept. Luckily, a Lv60 ME1 import lands you at Lv5-6 ish right from the outset, so that'll help a bit...still going to hurt. A lot.