One of the difficult decisions I had to make when going with Verizon is what phone to get. I have been a Windows Mobile user for quite some time. I really just stumbled upon it through chance and circumstance. But I quickly found out how it worked, found the software that I wanted to use for it, and never looked back. That’s not to say that I ever thought Windows Mobile was perfect. It was inconsistent and not ultra-intuitive. I had to install third-party applications for things that should have been native to the OS.

But when it comes to technology, I have a conservative soul and stick to what has always worked for me. I don’t like it when software-makers do massive revamps. They typically add features I like, but they change what I have always been delightfully accustomed to. And so it was with Windows Mobile. Windows Phone 7, WM6’s successor, is a massive revamp. None of the WM6 software will be compatible. Features I’ve come to rely on with WinMo will no longer be there, including multitasking and cut and paste. The unparalleled customizability of WM was explicitly dropped. In other words, they took half the reasons I will never own an iPhone and inserted it into their OS.

Because of this, I am left to find another OS. I didn’t think this would be that big of a deal as I thought of all of the things that I don’t like about Windows Mobile and thought that maybe Android, Symbian, or the Blackberry OS might not have these limitation. I was particularly interested in Symbian and Android, but it appears that Symbian is being gradually retired as well as its primary benefactor and owner, Nokia, starts looking for alternatives. It was looking at the alternatives that made me realize all that Windows Mobile could do and that I took for granted. I was relatively sure that I was going to migrate to Android for my next phone, but to my relative shock I discovered that Android can’t do a lot of things that Windows Mobile can do and has been able to do since at least 2003.

When it comes to smartphones, I have pretty specific needs. The biggest thing is what I call The Walkman Test. Basically, I want to be able to play music and videos without the device ever having to leave my pocket or holster. That means I need to reprogram the buttons both within the OS and within the media player. What I do now is set the volume buttons to open and start playing media. My main concern with Android is that it would not be able to do this. I was also concerned that, unlike with Windows Mobile, I might not be able to redirect all audio (and not just phone calls) to a Bluetooth phone headset. Any OS will let you use a Bluetooth stereo headset, but not necessarily pipe all audio to a headset designed mostly for phone use. Even Windows Mobile makes this a challenge.

I still don’t know the degree to which I can customize buttons on Android so that it can pass The Walkman Test. I asked some Android forums the question and got zero answers and a few “Why would anyone want to do that?” questions (which is usually a sign that it can’t). But I discovered along the way something more damning: Android can barely play my videos at all. I mean, it can play videos and there are tools to convert the videos into something that Android can play, but I don’t want to have to convert a video any time I want it to play on my phone. There are precisely two video players for Android that can play standard AVI files and both are crude and reports say that the video play is choppy (and one of them is in Chinese). This is in stark contrast to Windows Mobile, where there are at least two players that can play any type of video.

Perhaps more disconcerting is that the make-up of Android makes it so that it’s unlikely that any players will be coming out any time soon. I don’t know the technical details, but the folks from CorePlayer (the makers of both of the great Windows Mobile players) have said that they are trying but the Android OS is not at all conducive to third-party apps getting the kind of direct access to the hardware to smoothly play videos. I’m guessing that’s why the video on the players that do exist is so choppy. Android has to act as an intermediary of some sort and that bogs everything down. DivX, which also has a player for Windows Mobile, has flat-out announced that it is giving up on an Android player until Android changes its specs.

I have to believe that at some point Android will get it right. What I find fascinating is that I talk to Android users about this and they simply don’t understand why this is a problem. What’s so bad about converting videos? External video types can really drain the battery so it’s a good thing this option is not available to use (the same rationale that Apple defenders use for the complete lack of Flash support). Well, I’d like to make that decision for myself. I also get questions about why it’s such a big deal to have to pull the player out every time you want to stop or start a video. It makes me want to yell “Because this is what I want to do!” and I get agitated that everyone acts like it’s such an unreasonable request when Windows Mobile has been doing it for seven years.

I guess a lot of it just comes down to what someone wants from an OS. Which is what makes questions like “What is the best smartphone OS” ultimately dumb questions. I fail to see what the big deal is behind what the iPhone’s OS can do. I don’t understand how a sleek OS is worth not being able to install any application that Apple doesn’t want you to install (or having to go to war with your phone to do so). When people say “I love the iPhone because it can do x,” I am inclined to look at those people just as blankly as they look at me when I say that I like Windows Mobile because I can do y, which no other current OS can seem to do.”

Incidentally, I got a Windows Mobile phone and absolutely love it. It’s probably the last WM phone I will buy since it’s a dead platform. I am just hoping that Android can get its act together between now and then. Or maybe Windows Phone 7.1 (which, to its credit, will be able to play my video files right out of the box) will be a little less iPhoney. I’m feeling a little more anti-iPhone than usual. Not because the iPhone is a bad device, but because it was successful for all the wrong reasons. It demonstrated all of the things that a PDA OS can be successful without. And so Palm and Microsoft follow suit, throwing things like free-flowing software support out the window (no pun intended) and essentially dumbing the phones down. Making them easier to use, but making it harder to do anything outside the sandbox.