My headlight cuts out intermittently while I am driving. It will come back on if I squeeze in the clutch and push the starter switch button. I have replaced the right side handle assembly, thinking it was a bad starter switch, but that didn't solve the problem. It isn't a bump in the road that triggers it either because it has cut out when I am at a stop light as well. Any advice before I start chasing wires???
It sounds to me like the headlight relay in your junction box has gone bad. You can replace the junction box or you can bypass that relay. To bypass it, look at the 8 pin connector going to your junction box. You will notice there are only 7 wires. Move the blue wire to the empty slot, and your headlight will come on when you turn the key on, instead of when you start the bike. I've been running mine like that for several years with no problems.
One of the things I noticed with my bike when I was charging my battery between short rides, (bad stator had not been fixed yet), the light would go out or not come on when the battery charge got low, even though the bike would still start and run. Make sure your charging system is in good shape!