Colarndo,
You are suggesting that the equalization function of a booster (or any other gadget, for that matter) will nullify a compressor's function by "increasing dynamic range". And this, I believe is a fallacy. A booster SHOULD NOT affect dynamic range, even with EQ function. Think about this: many people use EQ after compression. Does EQ-ing after compression render the compressor pointless?
Also, from the way you talk about headroom, it seems that you believe every frequency has its "own headroom" and "dynamic range", which is not quite right. If you boost a certain frequency (EQ), it takes up some headroom. Dynamic range SHOULD NOT be affected. Both "headroom" and "dynamic range" describe the signal, not the individual frequency components.
funkygeos,
I don't understand why you would want to leave your booster permanently active. If you're looking to EQ your signal, I believe an EQ would suit the job better. If you just want to make your tone louder, simply turn up the volume!
Most people who use a booster need it as an "effect", either as a pre-gain to an effect (overdrive etc.), or as a simply clean boost of volume (after the effect). Or, perhaps, to amplify a low-output signal (usually passive basses) into a high-output one.
Like I've said before, and I guess many would agree:
If you need a simple boost of volume, put it after your comp.
If you need to get something wacky and experimental (depending on how you set your comp), put it before the comp.
In both cases, the booster should be turned on whenever it's required. To use it as an "always-on" effect simply for louder volume seems quite extravagant. Why not just use of the makeup gain on your compressor? Or... just turn up the volume of your bass/amplifier.
Bottomline:
Try everything out, and see what you like. And... share what you've found!