This is probably the most popular thread topic here (next to oil) and you'll find a LOT of stuff if you search a bit.
Basically the situation is that the electrical system has a power demand - the lights, ignition, and alternator field coil. There's also the electrical power supply - the alternator power coils.
Hopefully there's more supply than demand. The original bike when hew presumably worked fine and charged the battery, so what's changed?
1 - Age: the electrical connectors and switch contacts have gotten corroded and most probably have a higher resistance than as new. Nothing else really ages to cause a problem in the electrics. The trouble is that applying Ohms Law of electricity, a higher resistance in a circuit carrying current means a lower voltage at the output of the circuit. This has a lot of effects (stay tuned).
2 - Modifications: Nobody seems to install dimmer, lower power headlights - H4 lamps are popular, and finding a low power bulb to match the factory headlight draw is possible but rarely practiced. Lots of people add marker lights. 3 Ohm (stock is 5 ohm) ignition coils are a fairly popular "hot rod" modification. Adding to the demand when there's little extra supply available - the 350, 400, 500 and 550 are all marginal - will often lead to battery discharge or at least low running voltage and an inability to use the electric start regularly.
3 - Battery. No system will work with an old half-dead battery.
4 - Regulator: These are actually more reliable than most people think and are rarely the problem, but they do fail.
The cure? First, clean all those bullet connectors in the harness, and any multi-conductor connectors (engine plug, rectifier plug, fuseblock plug?). Shoot some contact cleaner into the ignition switch and exercise it a while.
Measure the voltage drop at your regulator with the bike all up and running.
Well. I've been writing this while sausages grill. They're done now. I'll try and get back for more later!