I may be young, but I think I have a couple to add to this thread. (which is a hell of a fun post, by the way...)
I had a royal enfield a couple years back and it gave me nothing but trouble. I ended up selling it after the third motor overhaul and more money into it than I paid. One time I was cruising on the PA turnpike (interestingly enough, on my way to a enfield dealer to get parts) and when I got off the exit went to downshift for the turn, and found that my gear shift lever had decided to take a hike somewhere between Harrisburg and Lancaster. I was stuck in 4th, pulled in the clutch and drifted off to the shoulder. Sitting at idle with the clutch in, I sized up my situation and remembered that the enfield has a neutral finder off the gear box. I reached down and adjusted it all the way out so if I hit it, it went to 1st rather than neutral. So I took off in first, and to shift, I had to reach down to the gear box and gently pull up the neutral finder and it would change to 2nd, 3rd, etc. Rode around like that for probably 500 miles till I got a new shifter. =)
Kicked my triumph till I thought I was going to have a heart attack and sat there sweating and cursing...saw a homeless guy and paid him $5 to bump start me =)
Was kicking that damned enfield and it backfired and shot the carb right off of it! Might have made it into orbit and still be there if it hadn't been for the throttle cable keeping it by the bike. Dried the spilled fuel with my shirt and Jerry rigged the boot with a coat hanger and plyers, and she started right up.
Broke this adjuster thingy on the clutch and it went missing. I knew I should have fixed it, but it had stayed in place forever and had forgotten about it until it was gone and found I couldn't use my clutch. Took a #2 pencil and broke it off and stuffed it down in there and found it kinda worked. Broke off several pieces and found one the right length for the adjustment I needed and worked fine. =)
Blasting up 15 when something didn't seem right, pulled off and found that one of my mufflers was gone! rode the wrong way on the highway back about 2 miles and found the muffler luckily in the grass, scrapped up, but otherwise not crushed. Got back on the road holding the muffler in one hand and trying to ride with the other, figured out quick that wasn't going to work. Eyed up the bike and thought I could figure out a way to put it back on or I could pull off the other one and leave them on the side of the road and come back for them... Ended up figuring out a way to mount it using license plate bracket and the bolts from the license and the chain guard.
Ahh....this is bringing back so many memories! I dunno how many times I have fixed wires and shorts and fuses with tape, paper clips, fabric, soda cans, misc springs, everything!