My Dad and I have a (June)1999 Bullet 500. Last Month of iron engines with the original 4 speed Albion gearbox. It leaks, you just buy the official, "ROYAL ENFIELD" embossed oil pan. It lubes the chain for you. You put thin grease in the gearbox (Or 50-50 mix of grease and 85w-140), or tear it apart and replace the bearings with modern, sealed industrial ones. I redid the electrical system with my own harness. These few tweaks (and a mikuni enrichener circuit carb) make it run great, with 15k on the clock so far. Cruises all day at 60. Rides up US 1 to Pt. Reyes are amazing on it. Very comfortable. Comparing to my BMW k75, it holds up with the new bike on back roads. The sewing machine bike beats the mine pump on the freeway, but that is what it is meant to do.
You take the bike for what it is. The new ones are nice, but treat them like a 250. They can handle the freeway, but they don't like it. They are 60-65 mph bikes, and you can cruise all day on them.