I don't really gamble at casinos. The last time I spent $50 at a casino was over 9 years ago. I have gambled on the stock market, though.
Anyways, my brothers and parents gamble at casinos sometimes. One brother is definitely down money over the years because he's not nearly as good a gambler as he wishes he was. My parents are near even, maybe up a bit - they play vert small stakes for fun. My other brother is up significantly because he plays a consistent game of blackjack with tight self control, usually.
As for your plan, if it's just straight up games of chance like slot machines vs. games of some mathematical skill, then you've got to accept that the statistical probability of you coming out a winner is quite low and that you're likely to spend your $100 before you leave.
Granted, one time when I was waiting for a seat at a blackjack table I put 75 cents in a slot machine, won $150, and quit for the night.. so, it does happen.
And one night last week, with a live guessing game at a new casino, my brother witnessed someone guess ten correct answers in a row to win $2 Million on the spot. True story.
So, yeah, if you accept that you're likely to spend $100 and you're okay with that for the entertainment value and the ambiance and chance to possibly witness some others' high stakes excitement, then go spend your time & money how you see fit. It's a hundred dollar night out for once in your life, not a thousand dollar a day gambling habit until you lose your house. Just do it, have your fun. 
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No

for supporting trump. Because doing so is deplorable.