I'd pay someone to protect kirk hammett from murderous people. I know you say the guy's over-rated and I know there are more technical and original players out there but I think some of his solos are seriously cool, Satch rated him as a good student.
As for shoes, don't ever judge a guy by his Buck (skin) cover!
I wear terrible shoes.

Seriously though.. a trillion's a lot of money. I'd buy myself a double neck (bass and guitar - Michealangelo style with necks at 120 degrees), through neck with synthesiser potential double floydd roses with a built in harp for cool drone notes.
Then I'd pay off my sisters debts, provide mother for a comfortable retirement buy a couple of houses, a motor caravan, driving lessons, diving instructions, more education (learn some scarier maths and physics perhaps) and then give the rest to OXFAM bar some put in the bank to acrue intrest.