Oh, geez...I've been in your position, and have done pretty much what you propose doing for a similarly-unmotivated, unaware, aimless young relative, and IMHO and experience, it ain't gonna work.
First, going anywhere and relying to any degree on a scooter or motorcycle is directly analogous to traveling on hoseback: Job One is to see to the mount, its care and well-being. A person with no track record for personal responsibility, no matter how likable, will not be able to do it.
Secondly, dropping a bagfull of "gifts" - tickets, scooter, training courses, travel subsidy, etc., - on a young person who has shown no inclination or interest in caring for and developing himself is only going to enable him in his unproductivity, as I found out for myself. The motivation, the sense of responsibility have to come first, else your 'gifts' are soon squandered and abandoned.
It's a tough situation and hard for families to know what to do - there seem to be more kids out there than ever before who are drifting, afflicted with aimlessness, unconcermed, relying on luck and the good will of others to get by. Simply giving them things and money does not help, and can indeed make things worse. Wish I had something more postive to suggest; I don't think your generosity is going to help this kid.
DR-Z400SM, '68 Honda 305, '64 Honda C110, '06 Honda VT750, GTS 250ie, Genuine 150, Vino 125, Zuma 125, Yam C3, Honda Met, Tomos ST, PCX 150, Honda PS250 Big Ruck, Vino Classic 49, Honda Rebel, and a Lifan CT 70 clone I forgot about...