I didn't wear my underwire bras for a long time more because I didn't want to stretch them out since Kate was nursing all of the time. It was super exciting when I started going out evenings and putting on a nice-looking bra. LOL I would say it's totally up to you. It's not a rule that you can't ever wear underwire, just be aware of the possible duct issue and if you have a problem then stop using them.

So I say try it and see if it works. Wearing a good-fitting bra can do wonders for the self-esteem, hehe.
(Oh and I have a horrible time with getting bras to fit too... it seems like I own way too many ill-fitting bras.)