I've found myself back in the market for a small smart phone again after my iMate Jam died from the numerous falls it took. (Note to cyclists, don't carry an expensive phone in a jersey pocket with food in it.) I sent back the Blackberry Pearl 8100 I was trying out a few weeks ago and am now on the hunt for its replacement.

My Phone and service requirements
I just want a phone that has email, web, calendaring and contact management and plays nicely -- syncs reliably -- with Mac OS X. Being able to read MS Office and PDF docs is a plus, I suppose, but not essential. Tethering either my MacBook or Lenovo Thinkpad are also possible uses I might consider useful, so cost for that service has to be considered.

Carrier service plans
I've compiled a cost comparison of service providers in the NYC area. This comparison looks for service packages that include the least expensive voice options and unlimited data from cell phone carriers serving the NYC area.

Note that there is a difference between Edge and EVDO service. Edge is capable of providing up to 200K upload at peak (more likely to get ~100K) while EVDO is capable of providing at peak up to 2.4mb upload (more likely to get ~600K). More information about Edge vs. EVDO at cnet. Also helpful was seeing this real world speed tests comparing Sprint and Verizon. I'm leaning towards Sprint after reading in bulletin boards that they appear to provide the fastest EVDO data service at the lowest cost.

Also worth noting is that choosing a Blackberry option would incur different costs. For example, TMobile has a Blackberry plan with unlimited data and 1000 minutes voice for $70.

Picking a phone
I have no idea what phone to use. Right now it's between the Treo 700p or 700w and the Blackberry 8700. The 8700 may be a viable option now since Daniel Pasco has come up with a solution for tethering a Mac to it, thanks to Alex for raising the bounty. Only downside to the Blackberry route is having to pay $4/month for proxy service unless you run your own, and I don't intend to do that.

I think I'm actually leaning towards the Treo 700p. Treonauts has a nice table comparing the current Treo phones. I know it's a downgrade (or maybe a sidegrade) from feature set of a Pocket PC, but I want absolute synching reliability and am willing to trade off some functionality for the peace of mind that comes with a Palm device talking to a Mac. I've had an iMate Jam Pocket PC phone synching with Mark/Space's Missing Sync and it's worked pretty well, but flaked out occassionally, requiring re-installs. My wife is now using one of the HTC Wizards (the 8125 on Cingular) and it seemed to be synching nicely, but MissingSync stopped connecting all the way all of a sudden this morning for her. Typical. I just don't want to waste time constantly tweaking my phone to get the address book and calendar synched up. I want something that just works and I can't wait around for the Apple smart phone that people have been predicting with confidence for over a year now. Of course, now that I'm ready to buy a new phone, I'm sure Apple will release the damned thing. Anyway, Pocket PC is out for me.

The only other real contender for me is really the Blackberry. I liked the push email, but am not sure I need or want to be that connected and available. After trying the Pearl 8100 for a week, I was also pretty unimpressed with the user experience. That Java UI that Blackberry users tout as simple and genius is a hierarchical mess to me. I'm a former Sidekick I, SK II, and PPC user so I have different expectations for ease of use. The SK UI is simply the best on any smart phone I've used. The PPC was fine because it was familiar, albeit in that Microsoft kind of way. And I wasn't very happy with SureType on the Pearl 8100. It worked remarkably well until you got to forms, especially password entry. There's no predictive typing for passwords, so you're left to do multi-tap entries there. Yuck. The real show stopper is that there's presently no Mac synching support with the Pearl yet. I'm tempted to hold out for the 8800, which will provide a full QWERTY keyboard and better Bluetooth support so we Mac users can tether using something like the Fibble.org script. But it'll still be a Blackberry experience and I've never synched a Blackberry with the Mac so I don't know how that goes, i.e. if it's reliable using Pocket Mac's software.

So I'm back to weighing the cost of experience vs. features and functionality, and what do I find myself looking at? On the surface, to a Mac user the Palm Treo 700p looks the logical choice -- the one running the Palm OS and not the Windows Mobile OS. But it's a step backward. If simplicity and reliability are the most important factors with all service speed and cost issues being equal, I personally think the Palm OS wins for now. That comes after trying quite a few smart phone OSes. But I also have to remind myself why I left the Palm platform in the first place -- I was an early adopter of the Treo, having owned the gray flip top 180g. The OS at the time was the reason I left. I couldn't have email, web, and IM apps running simultaneously. I don't think that's an issue anymore. One downside is that the 700p won't be upgradeable to the faster EVDO Rev A. For that reason alone the 700w might be more attractive or any of those HTC Wizard devices that every carrier seems to sell.

So anyway, I'm letting all of this information soak in for a while before I consider making the leap again. It's been a while since I've had to pony up extra dough for a smart phone, and for the extra service charges. Luckily my TMobile contract period is over so I can go the rebate route using Wirefly.

Any suggestions on the right phone to select for a Mac user would be greatly appreciated.