I think you need to take into consideration the health of your charging system if considering upping the wattage of your headlight (to a halogen, for example). The 500/550 makes just enough in stock form to keep the battery charged. If you do alot of in-town riding where you are not idling high, you are likely to drain your battery in pretty short order if you are running more watts than stock.
I was considering a headlight upgrade myself, but ended up installing a low and a high beam relay to power the stock Stanley sealed beam. It made a HUGE improvement in brightness. The old wiring, switches, and connectors on these bikes can all add up to voltage lost (i.e. loss of brightness) and you can counteract this by running power directly from the battery via relays. You might consider trying that first before investing in a new light. A couple of relays and some wire doesn't cost very much and may yield results that make you happy.
Good luck.