I don't know that I've ever been presented with this, but I only have 2 bikes - a 360 and a 550 (If you have one old bike, you'd better have two, one as a back-up) - but my next door neighbor has expressed an interest in "leasing" my Maxine, the 360.
He has a MC license, I know his mother and his wife, but I can't help but think this is not wise. For starters, he's not willing to buy it outright, and nor is it for sale. However, these bikes are meant to be ridden and I can only ride one at a time - I prefer the 550 for my daily commute. So this leaves a bike I adore, Maxine, sitting under a cover all day sometimes for a week or two at a stretch.
I keep telling him I need to do some more work, for safety's sake (and some of that's true) especially for a newb who doesn't know classic bikes. He is going to buy (allegedly) one of the repro Triumphs - and they're cool, I'll admit that - and basically, I think, wants my bike for practice.
He's willing to pay, and the insurance isn't too much of an issue - unless he gets killed on it, which is a huge problem - just wondering . . .
Anyone been posed with this before? And, if so, what do you recommend? My initial reaction is to say no - cuz a bike is not like "hey, can I borrow your car?" It's much more interactive and, as such, much more dangerous.
Gene