Go down to your local Harley shop and ask for the Screamin Eagle cam bearings. (Timken)
They cost me all of $18.00 for the pair and are cheap insurance although I dont think there are any problems with the later model stock cam bearings either.
As Bubbie suggested, have your heads machined for manual compression releases while they are off.
I had mine done ($180.00 parts and labour to do both heads) and am glad I did. Every once and a while, I forget to press em down before starting and am reminded as to why that was $180.00 very well spent.
Now that I am used to them, its just part of the regular start up routine.
The 103" kit with the 255 cams is a good combination and pulls real hard down low where most of us ride 99% of the time. The engine continues to pull hard past 5000 rpm but I usually shift long before that.
I was impressed with this 103" combo and its a pretty hard to beat for the buck.