So when recording dialog and testing it, I noticed that in-game my voices are much quieter and harder to hear than the vanilla Skyrim voice acting. I thought it was my microphone ( I was using an crummy microphone that came with a headset) so I went out and spent $30 on a decent microphone, re-recorded the dialog, and it's still barely audible.

I find that I have to take my recorded dialog and amplify it several times in Audacity so that it will be heard at the same decibel level as the vanilla Skyrim voices.

Is this what other modder's are experiencing? Is there something I'm doing wrong? Can other people hear their voices alright?

I had the same problem, I had to go into my recording device options in the tool bar and turn it up there.

Increase the volume to a reasonable amount, be sure to record at a decent gain as well, but not as much so that it peaks and distorts. Also, put a compressor on the voice, don't compress it too much though. And some EQing would do it good as well so it's not as disturbed by other sounds in game and so that it's clearer, but that'd require some ear and technique to do.