Update: Got in touch with Bob via his email address earlier today and he took care of whatever issue was up with my account. Now all of the events are showing up in my account with the correct Elite pricing as they're supposed to. Not sure if it had something to do with earning Elite due to # of days last year vs. purchasing - but either way, Bob made it right.
I'd strongly suggest if anyone is having issues that they contact Bob directly via email. While it might take a reasonable amount of time for him to respond (as he does have a full time job too, just like the rest of us) I'm sure he'll do his best to help out NESBA members and address the issues.
However, and I say this from experience in MY full time job, if everyone at the same time contacts Bob with questions/issues/rants-n-raves he's bound to get swamped. Just try to cut him some slack and be as understanding as you'd like someone to be with you if you were on the other end of the email.