It would only take eight losses to exceed the table maximum bet. It doesn't matter how many times you double up your bet. You will up you will only win five dollars if you eventually hit. This takes into account all your progressions up to that point. Even if you could exceed the $500 maximum bet, on the eighth bet you are risking $640 to win $5. You have already invested $635 for your previous seven bets. If you lose that one you are out $1,275. Can you imagine risking over a thousand dollars for a chance to win five dollars? The casinos know that if someone had unlimited resources they would eventually win. That is why the set maximum bets at the table.
Playing blackjack? Use basic strategy, if you can count cards better yet.
One of the fairer games that the casinos offer.
GL