I have always been a much bigger fan of boosts than overdrive. I was the only guitar player in my last two bands and it worked just fine. In my current project, however, there are two guitar players and there is more of a need to cut without necessarily adding a mountain of level. I started playing around with stacking boosts and overdrives and am REALLY happy with the way it sounds, particularly with Marshall style amplifiers.
I need 4 sounds for this project: clean, edge of breakup, crunch with a small level boost, solo boost. I ended up stacking the following into either Channel A of a Marshall or into one of my single channel amplifiers:
JCollocia Horus (low gain OD) > Way Huge Green Rhino > Bogner Harlow
All off is clean, the Horus cuts the bass a bit and adds dynamic gain (the gain increases with pick attack); the Green Rhino stacked with the Horus tightens up the tone even more and provides crunch. When I engage the Harlow (compression is all the way down), it gives a level boost for solos.
I have a strymon DECO at the end of the board which adds a bit of compression as well. The Neve transformer in the Harlow also adds a dimension that my Philospher's Tone doesn't have.
So whilst I still prefer using stacked boost pedals, in a two-guitar situation, OD definitely seems to be the better option for cutting through the bigger sound and frequency masking from the other guitarist.