My one "keeper" for the last30-some years has been my '76 "Ironhead" (not sure if that refers to the riders or these damn bikes) Sportster. I keep it for two reasons: first, it's just like the first street bike I ever owned (this one is actually the third, but I went through a Sportster per year for the first three years I had my license). Second, it reminds me how wonderful new(er) motorcycles really are. It really is a POS, but it's my POS.
Traditional bikes from that era - that of the big British singles and parallel twins, and American V-twins, are a whole different animal than what you are used to. They are literally their own worst enemies. The combination of poor materials, poor design, poor workmanship, and severe vibration means they just shake themselves to death. And leak like the Exxon Valdez. Most problems are traced to the former (you address the latter by continually filling it with oil) - some poor, over stressed part finally rattled and shook for its last time and just gave up the good fight.
So, yes, "bring tools" is good advice; I would add "spare parts" to that list. You won't have to ride it for long to figure which spare parts you will need to have on hand at all times. Unlike the old days when these POS's were new, you won't find parts locally. Hell, we used to be able to go into any Schuck's or NAPA store and find electrical parts for the old Harleys, because they were all Motorcraft or Delco anyway. We changed them so often that we all knew which old Ford or Chevy starter, generator, relay, solenoid, or whatever we needed. "I need a starter relay fo a '62 Ford F100..."
More good advice: buy a pickup truck, leave it full of gas, unlocked, and keys under the seat whenever you go ride the Royal Enfield. Never call the same friend twice in one month to go get the truck and come and get you; otherwise they get kind of tired of it. Never ride it further from home than they are willing to come and get you.
Have fun...
