These are by no means the only two phones that matter right now, but there are enough parallels and common ancestry (a certain John Rubinstein) to make this a natural first round of comparison. All the magic happens after the break.
Where Apple might need to catch up:
Apple was showing off what (at the time) seemed to be some pretty great push functionality back in June of last year, but since then Android and now webOS make Apple's implementation seem decidedly dated -- not to mention the fact that Apple still hasn't launched the promised functionality. Apple needs to make notifications universal (for whatever service and wherever you are in the OS), easy to act on and informative but at the same time unobtrusive, and they've got a long way to go on all fronts.
Developer freedom, transparency
Happily, Apple seems to be getting better at this as we speak, allowing a bunch of Safari-alternatives through today that would've been previously seen as a violation of its "no duplicate functionality" policy. We also just spotted a CoPilot GPS app running live on an iPhone, and it seems unlikely that a major developer would do all that work if Apple wasn't going to let it through the App Store. Still, Apple needs to do a better of job of being up front with developers, and stop making silly restrictions on the release of truly useful apps.
Apple only needs to look as far as the Jailbreak community to see some great multitasking in action, but hopefully it's going to take a look at what Palm is doing with its "cards" method of switching through apps -- quite similar to Apple's own tabs interface for Safari -- and give the people what they want.
Oddly enough, the Pre wasn't the first time we saw a device running this sort of contacts integration, 3's INQ1, a sorta-dumbphone from the UK, showed off this Synergy-style integration of social networking, IM and regular contact info last year. This isn't a new concept, and shouldn't be difficult to accomplish with most modern mobile operating systems, but for some reason Palm was the first company to manage to do this right in a smartphone OS -- we hope Apple catches on quick.
For a company that touts its own iChat app as one of the cornerstones of the desktop experience, Apple's been strangely reluctant to integrate IM into the iPhone, instead leaning on 3rd party developers to do it. The Pre shows that IM shouldn't be an afterthought, it should be tightly integrated into contacts and text messaging.
Ease of development with web standards
Granted, Mobile OS X has been widely touted for its ease of development, but we're surprised that Apple hasn't at least duplicated its own Dashboard Widgets -- which are just little self-contained WebKit-powered modules, with some similarities to webOS apps, minus the deeper OS integration. Is there room for a compromise here? The App Store isn't lacking for apps, but an increase in developers never hurt anyone.
Another feature that Apple could've easily ripped straight from its desktop experience, but Palm beat them to the punch. As the iPhone is saddled with more contacts, emails, bookmarks and apps, a universal search seems like a really easy solution to the problem of complexity. If nothing else, Apple needs to look at the number of steps it takes to perform certain important functions like making calls -- a bit less of bouncing in and out of the home screen could really do the body good.
We haven't seen a final version of the Pre in action yet, but what we did see seemed really wicked fast. And this isn't just about who can render the most FPS or scroll through a webpage better, this is about vehemently fighting off the general lag that can creep into an increasingly bloated operating system. Apple claims it's staving off multitasking to keep the OS responsive, we're wondering why our SMS screen is still loading.
Keyboard, removable battery
This isn't software, so it's sort of out of the purview of what we're talking about here, but we like physical keyboards, and we like the fact that Palm gives us the option. Some of us also like Apple's touchscreen keyboard, so we wouldn't mind Palm coming out with another device that just does touchscreen, and perhaps another keyboard device for the landscape-oriented among us. Since Palm doesn't have a paralyzing fear of buttons, pretty much anything is possible. Oh, and that removable battery is Just Good Sense.
Copy and paste
Where Apple's still winning:
Web-style development (with delightfully sharp claws into the OS innards) might be webOS's strong suit, but it also means webOS misses out on some of the incredibly powerful apps the iPhone is capable of. 3D games are the big one, but other things might be difficult -- if you haven't seen it done on a browser, you might not see it in your phone.
Apple's incredibly simple "this is the home screen, this button sends you there" usage model bests pretty much every other smartphone out there in so far as ease of use -- Palm might have to spend some time and money on ads and mindshare for its slightly-more-complicated gesture system to catch on.
Shall we count the ways? iTunes, MobileMe, App Store... Palm's probably right in thinking mainly about the cloud, but right now if you plug an iPhone into a computer, stuff gets done. Podcasts and MP3s zoom across, contacts sync, calendars compare notes. Not only that, but Apple is hard at work on a full-on web experience in MobileMe involving sync "in the cloud" from desktop to internet to phone and back again. Palm has chosen, perhaps wisely in many cases, to work with third parties like Google (Gmail, Google Calendar) Amazon (MP3 store) and Microsoft (Exchange) for getting stuff on and off the internet, but has no real answer to the juggernaut that is iTunes, or Apple's dexterity in this space.
Where Android is still winning:
'Nuff said? We don't want an IMAP client to look at our Gmail, we want the Gmail experience on our phone, whenever, wherever. Don't make us come over there...
Oddly, Google and friends have foregone the traditional benefits of open source like distributed development -- at least so far -- but picked up others, like the fact that the OS is free and can be put on any device you can hack it into. This is really great, and while we don't expect Palm or Apple to start giving away their OSs, we'd love it if they did.
This might be a toss up with webOS's notification style, but we're thinking Android's super-slick notification drawer might still have the edge here, both for unobtrusiveness and functionality.
Where BlackBerry and Windows Mobile are still winning:
It's not sexy, but playing nice with business back-end and IT departments sells phones and -- guess what -- there are a lot of people out there actually trying to get work done on these things.
Another element in the "getting work done" arena: if you want to edit an Excel, Word or PowerPoint document, you're probably not going to turn to a Pre or an iPhone to do it. Hopefully Palm announces something along these lines soon, they've classically been strong here, and it shouldn't be impossible to pull off in webOS, but right now the win clearly goes to Windows Mobile, with RIM a strong second.
BlackBerry's keyboards are legendary, and HTC's phones hit almost every high point you could ask for in design and form factors -- some people just need that landscape keyboard, or landscape keyboard + numeric keypad with a triple swivel, etc.
We know there's a lot of stuff that Windows Mobile, BlackBerry, S60 and even the existing Palm OS can do that have yet to be mastered or even addressed by the iPhone, Android or webOS, so consider this a placeholder for "favorite feature X" that you just can't live without, and be sure to bring it up in the comments!
Where we all lose:
We're not crazy people, we know why it's in Palm and Apple's best interest to partner with a carrier, but that doesn't mean we have to like it. AT&T has showed a continued inability to get 3G right, and a continued ability to drop iPhone calls left and right (granted, much of this could be blamed on the iPhone's chipset... whatever it is, it needs to be fixed). Meanwhile, nearly everyone we know has a bad Sprint service anecdote to share -- the carrier, while fairly strong at 3G data, has some serious problems, and those problems won't just go away when Pre users start hitting it up for bet-settling Wikipedia entries.