Don't feel bad
I've been working PT since 2003 and I still get bit on this detail. Ctrl-Z is my friend, as is switching to the grabber tools so I can just drop breakpoints and then drag as needed. When automating to get things even(like a bass track with a few weaker notes, or a vocal with some softer or louder words) I will alter the actual region("clip" for those in PT10). With 10, you have CLIP GAIN, but in 8.x, I would simply open the AUDIOSUITE Gain plugin and leave it on the screen as I listen down to a track. When I find a bit that's too soft or too loud, I will highlight it, adjust the GAIN plugin, and process it. The idea is to even out the volume BEFORE it hits the compressor(s). It gives you a more consistent "fit in the mix", and it hits the compressor more evenly, which is nice if you are using "character" compressors like SMACK! or softube's Tube-Tech plugin. This also makes it so you don't need as many volume changes with your automation