I've been cruising along with OS 10.3.9 for a while now, with no particular problems. However, I'm starting to feel left in the dust by the software world, since it seems some apps (like Safari) are only bothering to provide updates for users with 10.4 and up. And now Leopard--will that be 10.5?--is on the horizon, making me feel ever more antiquated.
Trouble is, updating an entire OS has caused massive problems for me in the past. The blinking question mark of death at startup; that kind of thing. This, along with the unwillingness to cough up actual cash, is why I've shied away from Tiger so far. But maybe I'm being unreasonable. Have you updated to Tiger? Is it OK? If I jump straight to the latest version (10.4.7) will everything be smooth?
However, I'm certainly not going to be in the first pool of testers for Leopard. No, sir. Braver souls can try that.