I think you’re making the wrong comparisons. If you buy $1 worth, you get p(win) U(jackpot) + (1-p(win)) U(-$1), which is more-or-less p(win)U(jackpot)+U(-$1); this is a good idea if p(win) U(jackpot) > -U(-$1). But under usual assumptions -U(-$2)>-2U(-$1). This adds up to normality; you shouldn’t actually spend all your money. :)
(Not really important nitpick:) The dollar is spent once the ticket is bought and doesn’t return even if you win, so you shoudn’t have there (1-p(win)) * U(-$1), but just U(-$1).
I think you’re making the wrong comparisons. If you buy $1 worth, you get p(win) U(jackpot) + (1-p(win)) U(-$1), which is more-or-less p(win)U(jackpot)+U(-$1); this is a good idea if p(win) U(jackpot) > -U(-$1). But under usual assumptions -U(-$2)>-2U(-$1). This adds up to normality; you shouldn’t actually spend all your money. :)
Of course you are right, silly mistake.
(Not really important nitpick:) The dollar is spent once the ticket is bought and doesn’t return even if you win, so you shoudn’t have there (1-p(win)) * U(-$1), but just U(-$1).