In general, whether 2 stroke or 4 stroke, you need to jet richer when opening things up. More air requires more fuel to keep the A/F ratio in a usable range and to keep you from doing bad things (like melt pistons and burn valves). 2 strokes usually come rich from the factory to keep Joe Schmoe from burning a hole through the piston running wide open for 5 miles down the side of the road in 40 degree weather. So leaner jetting is usually required to get the max performance for the experienced tuner / rider. 4 strokes generally come lean from the factory, usually for emissions reasons. Plus a 4 stroke can run lean much more safely than a 2 stroke. A 4 stroker will start to miss and pop when it gets way too lean. A 2 stroke will seem to "run better than ever" when lean, only to fail with an impressive amount of damage shortly there after.
Some mods let more air in and require leaner jetting. Boring a bike out is a prime example. The engine will have more vacuum on the intake (pulls harder through the carb), and therefore gives more signal or pull at the jets. A jet doesn't give one exact specific flow, it changes with the amount of vacuum the carb is seeing, position of the throttle, etc. Increase this pull and you actually increase the amount of fuel coming through the jet.
But again, generally you'll need to richen jetting when opening things up.