First call (well automotively anyway, as it wouldn't be my first priority) is a call to become a member of
AMP. Then there'd be an open call on here for the first annual DadHawk Track Day, Run What You Brung event.
I'd keep the FR-S and MomHawk's '05 Mustang (she wouldn't give it up, I've tried to upgrade her). We'd upgrade the family/vacation hauler from our '04 Suburban, but honestly not sure to what. A Suburban RST/Z71 would be tempting though.
Then I'd buy the GM Dynamic Duo for myself (C8 and a V Series Coupe) as my daily drivers.
After that, I'd have to upgrade my hangar before looking at some classic cars.
Not that I've thought about this or anything....