Off-the-cuff suggestion for specific PDA requirements, not smartphone

I've owned Casio PDAs, Palms, & iPod Touch (PDAs, never smartphones). On a number of occassions over the years, I embarked on web research to track down the Most Suitable PDA, but always got overwhelmed by the plethora of feature tables, lists, etc. It seems that research can determine suitability only to a very gross degree, and you really have to take the time to trial and get to know candidate devices to really determine suitability.

Obviously, that is unrealistic. Since my iPod touch is dying, I'm hoping to try once again to identify a replacement, but starting off with a very restricted list by surfing the crowd and getting reasoned suggestions for my rather unmodern requirements. If you can chime in with your off-the-top-of-the-head suggestions for the following requirements (and the reasons), I'd appreciate your input.

One of my unmodern "nonrequirements" is that I don't want to use a data plan because that ties my PDA options to a cellular provider and a contract. That's a whole new (constantly shifting) playing field that I'm not yet prepared to get smart about.

The mandatory requirements are:

* Calendar, contacts, & notes should sync with Outlook 2007 on
Windows 7

* WiFi browsing

* MP3 & WAV player

* Real keys in a hide-away keyboard

The would-be-nice features are:

* GPS
(do these exist on devices that aren't meant for data plans?)

* Maintains podcasts, updates episodes, track episodes listened to

* Entire top surface can be used for display
(as in the iPod Touch)

* FM radio

* Voice recorder

* Very marginal benefit:
Viewing videos (resident files & streaming)

An almost-nonrequirement is jailbreaking -- I don't intend to do that since I don't intend to spend lots of time getting to know the internal systems of the PDA. I treat it strictly from a user perspective, where it helps to me organize (and free up) my time rather than a hobby to which I devote time. However, jailbreaking is not entirely a nonrequirement because if the additional value-adding functionality is compelling enough and the time sink is small, I could go for it.

Thanks for any reasoned suggestions for me to looking further into.