Glenn,
As you know, the 255 cam is designed for low-end torque, roughly 2000 rpm to 4200 rpm. Unfortunately, the dresser duals and monster rounds are designed more for high-rpm horsepower, so this combination of cam and exhaust system is hurting you at both low and high rpm. If you switch to a header and muffler combo that is designed for maximizing low-end, the cam and bike can perform as designed, and while it won't be an all-out rocket, it will run pretty well. Of course, to maximize that, you'll need a real tune.
I'm going to assume (cough) you have the equivalent of the U.S. Screamin' Eagle Street
Tuner (SEST), which basically just allows you to use MoCo's canned downloads--which aren't a real tune. They are just "one-size-fits-none" generic maps that might be better than the stock map for non-stock exhaust systems. The only benefit IMO to the SEST and its downloads is that the dealer can charge you for a full dyno tune without providing one investing in a trained dyno tuner technician--and usually keep the bike street legal for emissions.
I have nothing against cam swaps, and have done them on about 2/3 of my bikes, but a compatible exhaust system for the 255, plus a real tune by a knowledgeable technician, might get you what you want.