Suggestions for a PDA

I missed an important meeting because I am too dissorganized. I wish to correct that.

I think I am too cheap to get a phone/data connection. I don't mind the initial expence, it is the monthly that I would mind.

I would like to enter the data on either my work or home computer then sync it up.

I have an ipod but playing music would be a plus but it would need to play by play lists/artist/album otherwise it would be worthless to me.

What should I be looking for? I have read past recommendations for HP. I would not buy a Dell.