I would have to think about the first one as in can I drink all I want beforehand you know till I blackout, so the next day I just bleed from the ass and have tons of money in my bank account. Hell I wouldnt ask any questions I have had worse...
And for the second one, hell yes. Also Fucking hell yes if it was after that one mysterious night when I blanked out, was walking like a penguin for a month, and had shit loads of money
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P.S. I would always say no to the time machine I know I would go back in time and just see a bar, pub, and or tavern and say "Cool, they had alcohol back then!", drink metric fuck tons of liqour, then some how headbutt someone important and screw up all of history....So no! Never ever would I want a time machine.