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you just didn't wager enough money at first.
it takes like a total of 5 grand in bets to level up the first time.
you don't actually have to win either, i leveled my skill to max just using the roulette tables with safety net bets, (bet half max on red or black, then put increments on other color numbers until all your bets have been placed, if it lands on the number you get a big payout, but if it lands on the other color you get your entire amount of money back,)