I've had both, and I desperately miss my Palm. I could download free applications that did everything I needed and then some. I could use standard batteries and they lasted for weeks. Navigation was easy and intuitive. The calendar and tasks did what they were supposed to.
My new iPaq requires resets almost daily. The calendar and tasks don't integrate, so I can't assign a time to a task, only a day. There is no way of hiding personal stuff. Snoozing alarms gives you limited time options. I've had it only six months, but it's already wiped itself out once. I fight with it constantly. It's supposed to save me time, not waste my time.
Here's the problem, though. BOTH Palm and Windows are trying to cram as much stuff onto these things as they can, and both operating systems are becoming more unstable.
Entry level, I'd recommend a basic Palm, maybe even something from eBay. I loved my Handsprings, or at $100, a new Palm Z22 might be a good first step.