With regard to the difficulty in finding qualified crews for sailing a clipper. I don't think that's an insurmontable problem. The large four-masted barques of the 1930's grain fleets were largely manned with young apprentices with very little sea time. It's true there was a core of experienced officiers and a small number of able bodied sailors to train them. I don't think it would be that difficult to form an experienced core group, just expensive.
But if it's expensive then the organizers need to plan some way to generate income to offset expenses, seek corporate sponsorship or sell film production rights.

It may be that some sailing vessels are too precious to risk at sea but I bet the Cutty Sark would generate a lot of interest. And it would be great to see her sailing once more.

I'm less sure that I'd like to the the Charles W. Morgan sail off for a whaling voyage. I do have some scruples!

Cheerily,
Charley Noble