It's been a gamble in my experience; sometimes it works, but at least half the time it doesn't. I suspect that PCGS as a matter of policy rejects a certain percentage of crossover candidates, just to enhance their reputation as a "tough" grading company. ICG, ANACS, and even NGC-graded coins are often deemed unworthy.
Case in point: I submitted a 1914 Barber half for crossover. It was in an NGC holder, graded Proof-64. NGC is also supposed to be a strict grader, right? PCGS returned the coin in the NGC holder with no comment. I then cracked out the coin and sent it in raw. This time they did grade it, as Proof-64 Cameo! Why wasn't it good enough to cross in the original NGC holder? Perhaps my coin just happened to pass through their grading process at a time when a "reject NGC coins" policy was in effect.
Nevertheless, I still attempt crossovers, because it does work sometimes and many coins will potentially command higher prices if graded in a PCGS holder. A few of my coins in ANACS and ICG holders have crossed.