1. Would definitely not work anymore. I'm not at all the type of person who says, "I need to work or I get bored." I frankly don't understand that person.
2. $300,000,000 @ 1% interest = $3 mil/year or $250,000/month.
3. I'd live well on $250,000 month and keep my $300,000,000 in the "bank."
As far as "luxury" items go...I'd buy a box at Doak Campbell and a box at Emirates Stadium (where Arsenal FC plays), w/season tix for 8-10 people to each place.
I'd still fly commercial back and forth to London though. For some reason I feel safer on a bigger plane. I'd just make sure it was first class from now on though obviously.
I'd also set things up to leave my daughter, my fiance, my mom, and my sister, each $10,000,000 in a trust that pays out 3%/year so that none of them would have to work again, but not enough that any of them could become total a-holes and have exorbitant FU money.
The rest I'd probably give to FSU and Cancer Research when I die.