I have an old shop that has made around 1 bil in profit total, yet I can't seem to get the achievement to trigger (I have visited my shop front, my sales log, and the "Profits" page). Is it broken? Am I going to need to make a NEW shop to reset what apparently got cleared while I was on hiatus and the new system went in?

Also, I have...several "Legacy" achieves I swear I USED to have before I took my break (it was a looooong break.), but they all seem to have reset, so am I just screwed on those, or?

I'm just slightly annoyed that I apparently have to redo all of these achievements I used to have...x_x

First before you start trying to redo your old achivements, you should submit a ticket. Achievements were imported from the old achievement system but incompletely. At that time we had to do some manual importing, but the links for that, and the old achievement pages are now gone. I don't think there is anything you can do at this point, but staff may be able to help you.

Anyhow, its worth a try before putting in more work.

For the Make a Living achievement, I think you have to go to the "edit shop" tab.