Just a short update on my Naxx experiences:

Yesterday I gathered up the will to wipe a bunch trying out new bosses in the spider wing in Naxx. After I cleared the trash PinotNoir (a regular poster on these boards) messaged me and asked if he could bring in a healer since he'd never seen Naxx. After cautioning him about the high probability of wiping repeatedly as I learned a new boss for the next few hours trying Anub'Rekhan down, he joined anyway.

Turns out we downed Anub down on the first try! Didn't lose a single toon and I don't think anyone's health even dropped below 50%. Of course, I had planned much longer for Anub, knowing he'd be tough, and Pinot playing a healer in blues and crafted epics helped, but given my poor early experiences trying new bosses I was ecstatic. I'm certain I could have 10-boxed it instead of 9-boxed it.

We then went on to Faerlina and one-shotted her as well.

Maexxna wiped us a couple times, then a couple more guildies joined us and we took her down, then we took down Instructor Razuvious for good measure.

Overall, a very encouraging night with some great gear upgrades for us and a lot of fun.

I would definitely encourage you to continue working towards 10-boxing ^^