I would prefer never to have to cash out... I'd rather have services pop up so that I can purchase things with my BTC directly.
Maaaybe (but just maybe) I'll cash out my initial investment when 1 BTC is valued at that price, just to "freeroll" the rest of the way.. but not even that's certain.

I mean... I don't see bitcoin as a "get rich quick" scheme or a ponzi that I buy into to eventually get out before the ship sinks. I see it as a potential future disruptive technology.. in which case.. why would I ever cash out?