When To Give Up?

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Why are you cashing out?

Starting from $100, you could build up to decent levels quickly. But only by using the money you win to move up levels.

If you keep withdrawing to drop down to 100, you will always be playing too small to even think about playing for a living.

On the other hand, everyone has a sweet spot for ROI. It may just happen that your sweet spot is playing $5 NL with a 100 roll. If that is the case, just play as a hobby and enjoy the $50/month or so you are profiting - and don't torture yourself about wanting to go pro.