Perter: Not necessarily. If the DAC is good, it should have no trouble recovering the timing (within tolerance, of course, since nothing's perfect, as Rockvirgo said) no matter where the signal is coming from.
Jitter's been heavily hyped by the high-end community, partly because some of them came late to the realization that it was important, even though the problem was well known among digital engineers long before the first CD player came off the assembly line. There were some high-end DACs designed without a reclocking mechanism at all. Most studies have shown that it takes a lot of jitter to be audible--more than you'll find in just about any single-box player out there. Things are a bit trickier when you're using two boxes with a digital cable in between, but it's neither complex nor expensive to do it right--assuming you know what you're doing.
Jitter's been heavily hyped by the high-end community, partly because some of them came late to the realization that it was important, even though the problem was well known among digital engineers long before the first CD player came off the assembly line. There were some high-end DACs designed without a reclocking mechanism at all. Most studies have shown that it takes a lot of jitter to be audible--more than you'll find in just about any single-box player out there. Things are a bit trickier when you're using two boxes with a digital cable in between, but it's neither complex nor expensive to do it right--assuming you know what you're doing.