Myco, my approach is similar in that I know a bit of what is going on, or how it is supposed to work at least, but for the most part I just use that as a starting point and home things in from there by ear. Lots of fiddling and trial & error.
Page, are you using RMS or peak detection for that bass comp?
The thing about pumping is that when using compression to tighten up the bass, I'm sort of using that effect to add some missing dynamic to an otherwise flabby and ill-defined bloated bass or kick after getting the overall level general right with EQ. Maybe I'm using the term pumping incorrectly and bouncing is a better description for what I'm shooting for here, where by contrast, pumping is more about the unwanted side-effect on the other frequency ranges outside the bass range being targeted (possibly appropriate as an effect for mixers but not what we want as a more or less transparent mastering tool)?
That's in contrast to the standard application of compression in reducing dynamics, and more of an odd cookie for me to get set correctly. I have a harder time getting it to work, and sometimes it doesn't at all, but as mentioned the attack and release settings working closely in rhythm with the music are key. Seems a game of letting whatever exists of the initial transients through before the compressor clamps down and lowers the level, then releasing smoothly before the next event to let it through uncompressed again. Possibly a good job for the bottom range of a multiband comp since the 'bounce' would be limited to that band alone and not 'pump' the other bands.
Matt, interesting to hear about Ableton (never used it). The device chain building aspect appeals to my way of thinking and I've always wanted an easier way to do that or at least visualize the signal flow graphically.
I can see arguments for EQ before or after comp. I sometimes do both, depending.. usually EQ before compression at the track level and afterwards at the master bus, simply because they fall in that order without rearranging things, and I'm usually working iteratively and addressing one aspect at a time then moving on to something else. But that's more of a practical workflow thing. Yet consider electric guitar rigs and processors. Totally different goal since it's all about imparting color, but where the EQ goes in the signal chain makes a big difference in sound and there is often an EQ stage both before and after distortion stages for instance.
It might be that controlling major frequency and level issues with one stage of EQ and dynamics before going on to fine tuning the more balanced result of that with other, more targeted EQ and/or compression settings is called for. Multiple small adjustments often seem to work better for me than one big adjustment.