For your wife, a Nexus One from Google is probably the best choice, as it is the most iPhone-like and will blend in well with her colleagues' iPhones.
A few notes:
The Android O/S can do voice and data simultaneously if the phone radio and network support it (the Nexus One radio is capable), but as I understand it T-Mobile's network can't do data and voice at the same time due to a limitation of their 3G network. Verizon cannot do voice/data together either, not sure about Sprint.
An unlocked phone will get most of your features, go to google.com/phone for the Nexus One (cannot be purchased anywhere else), which is unlocked, and has the best CPU (Snapdragon at 1GHz) and screen currently available.
I don't think bluetooth tethering is available on any current phone, but you should be able to write an app for it on an unlocked phone.
All Android phones can connect to your mail server if you load an appropriate application from the Marketplace.
All newer Android "Google Experience" phones can play vorbis and theora AFAIK.
Sync depends on software, look through the Android Marketplace for sync apps that match what you use on the desktop, or you could write your own (it's not very difficult).
All "Google Experience" Android phones should have GPS, camera w/ video, full function while charging, bluetooth, WiFi, compass, accelerometers, external storage (mostly SDHC-micro).
I don't think any current Android phones have external display capability
One of your desiderata confuses me:
Phone-to-phone via bluetooth/wifi (do you mean walkie-talkie, phone calls, contact sharing, or other?)
der.hans wrote:
> moin moin,
>
> I need to get new phones. Which of the t-mobile android phones best meet
> the following requirements?
>
> Required features:
> . bluetooth tethering
> . ability to turn off GPS if one is available
> . ssh out
> . bluetooth
> . connect to my own mail servers
> . root access
> . play ogg-vorbis
> . contact, etc. syncing w/ GNU/Linux
>
> Desired features:
> . tether and call at the same time
> . on phone internet connection and call at the same time
> . ssh in across cell network
> . USB tethering
> . fully functional while charging
> . root access w/o jailbreaking
> . wifi
> . tetherable via wifi
> . phone to phone communication via bluetooth
> . phone to phone communication via wifi
> . GPS
> . camera and video
> . external storage card, prefer sdmc
> . can use external display ( monitor and/or TV )
>
> Any features that I forgot?
>
> t-mobile has Motorola CLIQ, Samsung Behold II, t-mobile myTouch and G1.
> Which is the better phone? I will be trying to do this w/o a contract, so
> deals don't matter and all phones appears to be almost equally expensive.
> I am interested in consumer ready, easy to use as this one is for my wife.
>
> What services/features are included in the service plan? If not, what is
> the add on cost?
>
> . cell phone calling?
> . internet access ( not just web )?
> . tethering?
> . gps?
>
> I still haven't completely decided whether I will go with the Nexxus One
> or N900 for my own use. Will the N900 work with t-mobile? I believe it
> will.
>
> I could consider ATT if I go with the N900 and it works well with ATT, but
> as I understand it the Nexxus One currently will not work fully with ATT.
>
> Does t-mobile carry a Linux-based, large numbered, low-cost phone? This
> one just needs to be able to make and receive calls on the family plan.
> Receiving text messages on the family plan would also be good.
>
> ciao,
>
> der.hans
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