I currently use the Samsung Saga/i770 with Verizon (and the Samsung i760 before that). I am completely and 100% addicted to Verizon's OTA sync abilities with Outlook. I will never own another phone that doesn't have that capability. Specifically, I love the fact that I can update a contact or calendar item on EITHER my device or my PC and it simply appears on the other within a few minutes.

My wife desperately wants an iPhone, so we're thinking of switching to AT&T. My question is this: Is there any other provider that offers OTA sync with outlook? With Verizon, it's easy, just a little sync app you install on the PC and it takes care of everything. My understanding is the iPhone doesn't do OTA, you have to manually sync it. And I guess Blackberries do OTA, but you need to be running a Blackberry Server. I could theoretically do that, but don't want to deal with the hassle if I don't have to...

My only other big factor is that I really like Windows Mobile. Have tons of software for it, and it works great. I'd be willing to switch to a different OS, but would need full outlook sync capabilities.

Here are my answers to the required questions:
1. What PDA and/or mobile phone do you use today?
Samsung Saga/i770

2. Are you locked into a mobile carrier (i.e. Verizon Wireless, Sprint PCS, etc.), or do you prefer a particular carrier? Do you know if one carrier has better coverage in places that you need to be? (PLEASE SEE THE CARRIER NOTE BELOW)
Verizon, but I'd be happy to switch. I live in Boston, everyone has good coverage here.

3. Where are you based? Do you stay in one place or travel a lot? Do you travel internationally... how much and where? Do you intend to use your PDAPhone there?
Mostly in Boston, with some travel abroad. World Phone would be nice, but not absolutely required.

4. Do have a preference of Palm, Pocket PC, Symbian, Smartphone OS, Blackberry, etc.?
Windows Mobile is nice, but I'm open to whatever as long as it has OTA outlook sync.

5. Are you likely to run it the way it came out of the box, or do you intend to load a whole lot of extra applications and stuff on it? Do you know of anything now that you will need to run?
Lots of other apps if it's Windows Mobile. Specifically Photo Contacts Pro, iLauncher, S2U2, Weather Panel, Sprite Backup, Live Search, Google Maps, Pandora, DUN (I think the program is called Internet Sharing). If not Windows Mobile, need some kind of photo caller ID with ringtone grouping.

6. How important is wireless data access, and for what would you use it? (i.e. Web browsing, VPN, Remote terminal Access, Instant messaging, etc)?
Web browsing and DUN are key. Don't need VPN, remote access or instant messaging.

7. Will you need to view Microsoft Office documents on the PDAPhone? Will you need to edit them?
No.

8. Will you need access to an email system?
a)Is it corporate (Exchange, Groupwise,Lotus, Other?) What Version? Do you want email wirelessly or do you want to do it in the office with a sync cable/cradle? Can you get your Corporate email configured for mobile access or do you need to run a desktop redirector?
b)Is it Pop3/Imap? Who is the service provider?
Wireless email is cool, but not necessary. Would use POP3 or IMAP probably. Would probably need a desktop redirector unless there's a free server client I can install on an XP machine I have that's always on. I'm open to that if it's easy to sync between my phone to the "server" AND my PC to the "server."

9. Do you do SMS messaging a lot (telephone to telephone messaging)?
Yes, a lot. Must be threaded.

10. Do you want to use a GPS with the PDAPhone for mapping and navigation?
I don't know, but would love to.

11. What is your size preference.. very close to the smallest cellphone, or you don’t care.. function over size?
Don't care. Function over size.

12. How will you carry it... pocket, belt, purse, etc.?
Pocket.

13. Do you prefer a particular form factor… flip-phone, candy bar, etc?
Doesn't matter.

14. Do you prefer a QWERTY keyboard, numeric dial-pad, or stylus?
Would prefer QWERTY keyboard. All touch screen kind of freaks me out, but if everything else fits, I'd be willing to give it a shot.

15. Do you want to play a lot of video games on the PDAPhone? What kinds - puzzles, strategy, action adventure, etc.?
A little, mostly low-res old-school games. Not a huge deal.

16. Do you want to listen to music on the PDAPhone? What kind... mp3, streamed, etc.?
Not necessary.

17. Do you want a camera on the PDAPhone?
Doesn't matter.

18. Do you have any other hardware you intend to use with the PDAPhone? Do you intend to use any Bluetooth devices? What types of devices?
Bluetooth headset would be nice, nothing else, though.

19. What kind of battery life do you need?(Always near a charger, battery life is not an issue or Need the battery to last several days) How many hours do you expect to spend talking on the phone? How many hours of data?(Web browsing, push email, VPN, IM etc)
Doesn't matter.

20. What are your budget limits (PDAPhones range in price from below $100 for older used models to nearly $1000 for high end models without a carrier subisidy)?
Doesn't matter.

OTA sync is more a question of "how" rather than "does it exist." There are a number of low cost mail providers that support MS Exchange, and that provides OTA syncing. On WM platforms, there are also apps around to sync to GMail OTA (probably for the iPhone as well, but I don't know for certain). If you ask around for opinions on the in the Lounge, I'm sure you'll be pointed in the right direction for what you want.

If you like WM and are looking at AT&T, I can highly recommend the Fuze (particularly with the updated ROM they released). Good performance, lots of RAM, microSD expansion, GPS, Voice Command, A2DP support. Very solid phone that I expect to have a good long time.

If you don't mind spending a bit more, getting an unlocked Touch Pro 2 might be interesting as well. It may not support US Data networks, though, so check the specs carefully. Rumor has it AT&T will be selling the phone, but be warned that HTC & AT&T can combine for some wonky first passes at phones that get fixed with later ROMs. AT&T wants their stuff on the phone, and that seems to leave some things that should work better a bit broken.

Good luck!

The only problem is that I want simplicity: Small app on my PC or "server" (just a box running XP Home that's on all the time) that syncs OTA directly and automatically to Outlook and my phone. GMail OTA (if I'm not mistaken) has another step: Syncs your phone to your gmail, but then you have to sync your outlook to gmail, one more step than I want. I'm also not running Exchange, and don't know if I have a PC capable of it (and it's like $700!).

Basically, right now I have a 10 MB app on my PC, and that is ALL I have to do. That's it. Phone syncs to outlook automatically, and vice versa. THAT is what I'm looking for. Any thoughts?

You don't need to run Exchange yourself, there are services on the Internet that do that for you. So you sign up for one of those, have it grab mail from the accounts you want, and then that syncs to your phone. It ends up aggregating your mail at the Exchange service for you. You can do the same thing with GMail or Yahoo where they'll log in to other mail services and collect all your mail. Then use either IMAP or POP to sync to your windows mobile device.

That's got a pretty significant advantage for you personally - you don't need to leave a personal computer running to sync with. I personally never understood why folks liked the "Sync to my Outlook" apps because it means your home computer can't be off and it has to run the software you're mentioning. My phone syncs to an Exchange server for work, GMail, and two other mail accounts and I don't have to leave a computer on. If I gave up on the Exchange server, I'd switch to syncing contacts with GMail using an Outlook connector app or one of the services that's running around to do that.

It's not all that hard to replicate what you're doing without the additional application is all I'm saying. You just need to look for the right mail service and/or add-on to make it work. There's literally no need for that 10MB app on your machine, but since "it's easy" the carriers provide them to reduce churn.