I'm on my 5th one- I have always owned Palm based. My last few had all of the bells and whistles. My new one is the base model- Tungsten E2.
That said, I would suggest geting a bare bones one for the first one. It may not be for you, and if you go cheap, it may not be as painful when you leave it in a drawer to collect dust.
I can't live without mine. I have not, with the exception of a sony model, every had one die, I jut decide I need a new one. Mine goes with me EVERYWHERE. I am lost without it. It has my entire life all in one place. Phone, Calendar, address, appointments- and, most importantly, pics of my Daughter. It gets backed up on my desktop, so if it does die, I have a way to restore it.
My wife, on the other hand, used hers for about 2 weeks, decided it wasn't for her, and it sits, collecting dust. She is the type of person that likes a yearly planner, and uses that.
No help picking one, I know, but I go palm for the simple reason- how many times a day does your pc crash? My Palm doesn't. Ok, once or twice it gets a bad program. You hit the reset button on the back, and away it goes.
M