Which cams did you go with?? I've been considering the SE-255 as they seem to provide better performance across the whole Torque/Horsepower band. I'm also interested in knowing what specific changes you made to the primary gearing. I think, after doing a lot more research, that those two modifications will give me the best "bang for the bucks"!!
My preference in cams were the Andrews 26H. You will find the power range between 1800 and 4300 RPM's. That is where you normally use/need your trike power. At 3000 RPM's the motor runs like a sewing machine and really responds to any commands. Cams are a personal preference but in my experience the 255's are more hype than pull but again, that is just my opinion.
Now.. asking anyone if they know the answer to this... did HD change the 255 overlap after 2007 to become more smog efficient? I know the pre 2007 or 88 ci motor 255 cams were based on high performance in the mid to high RPM range. If they did change them I would go with an aftermarket but that is just me.
The best person to ask for the primary gearing down would be bdn56 as we just did this cam change and dyno to his trike. He also installed the compensator sprocket kit to reduce his gear ratio. I changed the front belt sprocket and had to install a device to adjust my speedometer as well and had to go to a smaller belt. With the compensator gear change you don't need to do any of that. He will be back from Thunder Beach in a few days.
As far as "bang for the buck" you are right on track but you will need a good fuel management system tuned by a good tuner. I know you have pipes and a SERT. The tune is only as good as the tuner. I would suggest a non HD dealer such as an independant tune guy as he can do more with your SERT than HD will allow. Do all of your motor work first, get it tuned then trike it. The SERT map should not change. If you trike it first then finding a dyno for a trike will be tough.