I am sure I am not the only person who has nurtured a few younger riders along the way. Sold one smaller bike I knew I was not going to get to for a very nominal cost to a father so he could rebuild with his son, great idea I say. I have one of my grandchildren interested but he is only 7 and his mother will have to be won over I am afraid, quite a daunting task. I will get there in the end.
I have rebuilt two motorcycles these past two years with the help of a young interested rider and her father then gave her the first one when we were done and her dad and I have another bigger bike planned for this coming riding season. Okay these are not big ticket bikes but she is just starting out and needs to start somewhere. She lusts after a couple of my very expensive bikes that she cannot afford but so desperately wants to ride, and here is where I see the dilemma you mention Mike, I want to see someone interested rewarded and because I can afford it will probably gift her one of those she so desires like the Triumph Daytona Twin.
There is a local member of the Classic Club that is "only about the value" of his collection and would not imagine letting something go to keep the hobby and interest going and that I think is sad.
I was lucky enough to get something pried from the grip of a Vincent owner lately, have established a good relationship and now I have brokered a deal for something quite exceptional for a good price to another younger enthusiast.
I certainly hope I am not the only one doing things like this to help younger interested riders.
'51 SQ4, '37 VH500 Red Hunter, '56 SQ4 (basket case), '49 Sq4 (basket case), '48 A7 BSA Twin, too many other BSA's, Norton's, Triumph's, Ducati's and Japanese to list. Just crazed is all my problem is.