The likelihood that you'll cash depends on your relative skill level. The more you're outclassed, the luckier you'll have to be / the hotter you'll have to run.
Frankly, unless you have reason to believe you're reasonably competitive at the $100 level, I'd try to satellite in rather than buying in directly. But that's me. If your BR can afford to take a one-time shot at that level, it's basically a matter of your discretion if you choose to do so.