Ya know I think this is starting to become a reoccuring problem. When I took my MSF course at the beggining of the year we learned on 05 Rebels. My BRAND NEW 5 mile on the clock Rebel supplied by the MSF was absolutly impossible to shift from first to second, you literatly had to give it a very hard kick and lift up off the seat to get it to shift, I mean a hard kick like kicking a soccer ball, this caused considerable ankle strain. This also was happening to another student in my class.
The instructor gave us new bikes the next day, no problem just a small tap and it shifted like it was supposed to.
Also, my buddy had an 04 rebel and had the same problems, He took it to the dealer and they fixed it. I don't know what the specifics were though. I have also heard at least 6 or 7 stories on the net with people having shifter problems on their rebels. I think Honda has a recall issue on their hands.