From what I've read those 255's could make the problem worse. Either of those Wood's cams will help performance and from the dyno graghs I've seen they are so close to each other I'd flip a coin as to which I picked.
I don't understand why you don't just put in a HD starter, there are plenty of choices on the market these days, wouldn't that cure your problem without tearing down the engine again?

 

I had wondered about that as well but I figured costs are not that much different and if I can solve my problem and get more power then why not? Also what do you mean by making the problem worse with the 255? you mean I might lose power by changing the compression or that 255 and headwork would cause more problems starting? If it is the latter wouldnt that get fixed by manual compression releases?

 

The 255 will work in a 103, and compression releases are highly recommended. The starting shouldn't be an issue, but whoever tunes the bike will have to be aware of pinging. The 255 makes a ton of low end torque by closing the intake valve early and building a lot of cylinder pressure. One member here did the SE 103" at 10:1 and was over 200psi in each cylinder....

 

I did the HD 103 stage 2 with 255 cams but no head work about 30K miles ago. Lots of low end torque but I did have some hot starting issues. A good tune by a pro helped a lot but the final fix was a SE compensator. If I were doing again I would probably do CRs but I would not let the dealer do any headwork unless you can verify they have the right tools and an expert to use them. You may want to try the SE comp before removing the heads again; it's a good addition even if you don't have starting issues.

Another thing that helps a lot is on hot starts, hit the starter as soon as you turn on the ignition, don't wait for the fuel injection light to go off. I read that here a while back, I don't know why, but it sure makes a big difference.

 

What's everyones opinion on Short Block Charlie in Tempe AZ.? I'm about to send my heads that way and let him work them over.