[Gogar]

If he's not handy I'd suggest you steer him towards the vintage look as opposed to an actual old bike. Any 21st century triumph would be great; 2009 or newer (fi) would be even better.

If he "knows nothing" then I really think he would love to crash a current bike as opposed to an old one.

If he wants an actual vintage bike I'd suggest a mid 70s Honda. Simple enough, with lots of parts availability and not very many special tools required.

If "tools" for him means pliers and a hammer then forget about it.