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I’m done with iTunes and iPods and iWhatever.

Last night, courtesy of the fine folks at Amazon.com’s shipping department, I received a 16GB microsd card for my Nexus One phone. I’ve been really looking forward to moving the rest of my mobile experience to the Android platform, which has really become an integral part of my life over the past couple of months. I use it for virtually everything now, and I’ve finally discovered what people must mean when they talk about a smart phone. Google has come a long way with Android since I wrote this article.

In addition to becoming my main email/news/web surfing platform, I’ve started using some of the media functions of the phone (which, incidentally, are among the weakest of the Android offerings), migrating them off of the iPod. The first thing I did was load up Google Listen for managing podcasts. Then I started using booksshouldbefree.com to fill up my audio book addiction until Audible get’s their act together and releases an Android client. The only two things remaining? A Bluetooth interface for my car stereo (where I do the majority of my listening), and moving my music over.

I’m currently using a 32GB iPod touch, and prior to that, I was using an 8GB Nano. That’s where it gets tricky. My music library is about 60GB, so I had to find some way to pare it down to the essentials. I am NOT a random music listener, so I finally settled on picking the songs I know I want on my music player, no matter what. I added a comment of kris_ipod to each track, and then made a smart playlist inside of iTunes that sync’d that to the player. Add in audio books, podcasts, and a second smart playlist to add some random filler and that took care of things. As I moved forward into larger iPods, I made larger random lists, and the core list grew as I added music from Amazon’s MP3 store (clean, unencumbered, play-it-anywhere music in high quality, fully tagged MP3 goodness), but I made a habit of making sure that all of my music that I wanted available to me on a mobile player had a comment tag.

Meanwhile, last time I reinstalled iTunes and imported my library off the server, it started an annoying process of “normalizing” my volume – essentially trying to make every track on an album the same volume. It’s a process that takes forever, and no matter how many times I cancel it, it just starts back up when I launch iTunes. At some point, I finally decided to just let it run. Since the setting for “Don’t Do That” didn’t work, I figured I’d just cave in and let it go, just like I did with the equally annoying “Downloading Album Artwork” feature.

To shorten the back-story, let’s say that everything worked fine up to a certain point. I copied the existing card’s content over to the new card, booted up and tested a few key apps to make sure everything looked good. The speed was great, and all of my data was there.

That’s when everything went south.

I still don’t have a good solution in place for syncing my music over to the Nexus, so I decided I’d just do a Windows search against my library for everything with my tag, and copy it. When I did the search, I came up with a number of songs that was about 1200 less than what was on my iPod. After about an hour of trying to pin down the problem, I checked a couple of individual files on the server and realized that while iTunes shows the metadata as being correct and what I anticipate it to be, the actual metadata in the files was overwritten with a volume level code in the comments field, completely overwriting my own comments.

Thanks iTunes. Thanks Apple. Now I have to go back and redo that entire effort so that I can move my music. I am literally talking about hours of work, unless I can pinpoint where you decided to screw up my files and restore them from the backups.

I’d like to point out that my music library is METICULOUSLY maintained. Every single track has album artwork and correct tags. I did that external to iTunes, and I don’t want it dicked with. If you’re going to do that, do it in your own damn data structure, not in the data structure of the physical files. Also worth noting is that fact that all of the music I bought from Amazon has now had the fingerprint comment overwritten.

Why did Apple feel the need to do that? I’m glad you asked.

It’s because Apple firmly believes they know what’s best for you. They want to tell you how you should listen to your music, how you should organize your music, and how you should access your music. They know best, and that’s how you’re going to do it. You won’t move to another platform ever, so why should you care if your files are damaged? Don’t worry your pretty little head about it – we’ve got it handled and we’ll show you what you need to know.

I won’t lie to you, Marge. I love me some Apple hardware. iTunes, on the other hand, is one of the worst-designed pieces of crap on the market. It constantly adds crap that it decides you need (like, you know, a whole new web browser and an auto update mechanism and a new network protocol), whether you want it or not. Don’t worry, we’ll tell you what you need and you’ll be happy.

Apple builds a really beautiful walled garden. Once you’re there though, good luck getting out with your data intact. They cleverly conceal a number of locks on the gate.

Consider this my “Dear Jobs” letter. In a time where we are overwhelmed with choices in mobile media players and the software to manage them, I don’t have to settle for a significant other that never listens to me, tells me “Pipe down sweetie pie, the men are talking. We’ll tell you what to giggle at”, smacks me on the ass and sends me to the kitchen for pie.

Sorry Apple, it’s not you, it’s me.

Let me start this by saying up front that I have used an iPhone for about 10 minutes, and that was to send someone’s pictures to a website for them. So, I’m not going to get into how great it is. I do own an iPod Touch, and I will state for the record that I think its interface is top notch. I’ve heard from a number of sources, however, that email is problematic on the iPhone, though supposedly the iPhone 3g corrects a lot of the perceived problems. Since I’ve never owned one, I don’t really feel like I should get into the relative merits of the iPhone, other than to say I’ll gnaw off an arm before I’ll go on the AT&T network – which, taken with the fact that it doesn’t work for Exchange in my environment, pretty much nixes my option of ever having an iPhone

I owned a T-Mobile G1 (the Google Android phone) for three days before returning it. I could go on and on about all the positive features that Android brings to the table. It’s a slick phone OS, considering it’s a version 1.0 release. I’m impressed, and you can bet I’ll be following its development.

I currently use a Blackberry Curve 8320 from T-Mobile. It’s my primary phone. I got it as part of a pilot program from work, and decided that since I hate carrying multiple phones, I’d just go ahead and make it my primary. It’s a stubby, not-at-all-elegant piece of hardware. It’s too wide to use comfortably as a phone without a headset (for which I use the incredibly elegant Jawbone gen 2), the screen is too small for video use, the camera is sub-standard, and it’s generally a temperamental piece of crap.

Having said that, why do I continue to use and love my ugly little baby?

Simply put, it just works.

I have some rather specialized needs from a phone if it’s going to give me my email and a pseudo-online experience. I have one Exchange email account, and 4 Gmail accounts. I need to receive email on all of them as near to real-time as possible. I do not want to get an alert 5 minutes after it’s been generated. I need it as soon as possible.

You can imagine that I was really anticipating the Android phone, even more so when I learned that it would be available on T-Mobile’s network first. Lots of people have complained about T-Mobile’s 3G network, but I didn’t encounter a single hitch with it. It was snappy and things loaded quickly for me. It helps that Atlanta is saturated with TMo’s 3G.

My enthusiasm quickly diminished from the point where I actually purchased the phone. First problem is that it’s locked to one Gmail account. From a technical point of view, that’s not entirely true, since you can add up to 5 other email accounts via POP or IMAP. Those four accounts, however, are fetch email, as opposed to push, and the fetch cannot be set lower than 5 minutes. Strike one. I need all of my Gmail to be pushed to my phone.

I thought about trying to work around it by setting all of my ancillary Gmail accounts to forward into my primary, but that’s where the Android hit strike two. Despite being an OS from Google, there is no provision for doing a send-as in the main Google account. So, I can’t even do a half-assed workaround to get past the problem. That’s just plain inexcusable. Google controls the OS, Google controls GMail – Google should be mimicking every function on the web interface. If they can code in the keyboard shortcuts, they can code in the send-as. I can only assume that this is a feature that will be forthcoming in a service release.

The next strike was when I realized that, since the phone is tied to one GMail account, I wasn’t going to be able to use the Google Apps (spreadsheet and writer) from multiple accounts. That’s a big problem, as was the realization that I’d only be able to use one of my Google Talk accounts (A problem for me since I chat on one, and do ping.fm updates from the other). Strike three, and the G1 is OUT!

My Blackberry is ugly, but it works. It has neither an interface as pretty as a G1 or an iPhone, nor any kind of rich ecosystem of apps like those phones. Really though, how many tip calculators or flashlights do I need? I can calculate a tip in my head, and the bright white screen on my Blackberry lights up enough of the room so that I don’t stub my toe in the dark.

In exchange for those minor issues, I get my Exchange email, and all of my additional GMail/Pop inboxes pushing email to me as soon as it hits my mailbox. I have apps for Facebook, Twitter, and Flickr. I have a couple of neat games, and some decent themes. I can’t really say I need anything more than that from a handheld device.

I went into the purchase of the G1 knowing that it would not do Exchange in my environment without going through OWA. My criteria for keeping the phone was simple – if I’m going to have to work around not getting my corporate email (which is important, since I use it for monitoring servers and environmental at work, for which they pay me), then everything else was going to have to work perfectly out of the box.

I’m not the only one grousing about this, either. Google’s lack of understanding about how a lot of people manage their email will harm them in the near-term, I think. Until they get with it and add support for multiple accounts which can interface with multiple services, and figure out a way to get Exchange email, the Android will remain an enthusiast platform, with no real chance of invading RIM’s turf in the Enterprise.