Technology To-Do

I've been thinking that a new laptop is not the only thing on my horizon that needs replacing. My phone is even older (is that possible?) than my computer, I think. A year or so ago it was having some problems with turning itself off, but that stopped.

(Phil, do you want that phone back that you loaned me when my cell problems were happening? It's sitting in a drawer over here and HAPPY BIRTHDAY, CHAMP!)

I also have a PDA, of the Palm sort. It's total bottom of the line, about 2 years old, and fading. It doesn't always like to turn on.

Phone/PDA combos aren't new. Of course not. I, however, am new to them.

What I want:
• Ease of use
• Ability to keep backup data at home (mac) and at work (PC) and possibly even somewhere online--easily. Calendar AND contacts. And to sync them with my email at work. And understanding how to do all of this because I'm kind of clueless.
• Good reception and hearing quality
• Not too spendy. (<$150 if at all possible)
• Easy to input data. FWIW, I've gotten adept at Graffiti, and so that's not an obstacle. If you have to input it like you would sending text messages, well....

What I don't need/want:
• Top of the line
• Status
• Flip phone. Unless someone can convince me that they're not as annoying to use as they seem to me.

Other considerations:
• Palm software doesn't play nicely on a Mac. It works OK, but it doesn't let me put enough information (directions, etc) with the appointment slot. There's no "Note" field on the Mac version.
• I have no contract with my carrier, and so am free to migrate. I've been decently happy with my carrier (AT&T then Cingular and back to AT&T), as far as service goes, and the one work cell I had with Verizon service sucked. No reception. Ironic, no?
• At work: My work email sucks. We have to use Outlook. I get more spam than real email. We don't have an IT person to help set this up. I've downloaded other mail software, but I don't know how to set it up (slightly pathetic).

Ok. Running off to an auction now.