I have an iPod Touch, but thank the gods I didn’t buy it, work provided it as a test.  I am disappointed and frustrated constantly by this thing, and had I purchased it myself you had best believe Apple would have given me a refund for it.  While it teases at being an amazing device that combines MP3/ media player, PDA, wireless device, etc in one slick slim little touch based toy, it fails on many many points.  Here is why it’s not worth the cash:

1. Unlike previous generation and “normal” iPods, the Touch can not be used as a USB disk.  This is a massive failure, and the iPhone suffers from the same problem.  I have no idea why, on the top of the line products, Apple removed a massively useful feature.  Further, Apple prohibits 3rd party software makers from allowing this to be done.  The only way you can use it as a storage device is to use some kludgy wireless disk app which is slow, unstable, and very very limited.  My old iPod could be used as a boot device for a Mac as well as mounting as an external hard drive.  The fact that this is removed on the Touch is unforgivable and instantly should knock off half the price.
2. Getting video on the device is very difficult as it must be in a very particular format at a particular size using a particular codec and framerate, etc.  Finding an app to convert your video to the format used by the Touch is difficult at best unless you want to pay for something that Apple should have provided for you.  The Mac can play tons of video formats, it should convert them for the iPod/iPhone automatically when you drop them on the device.
3. Getting pictures on the Touch is nearly impossible.  What?  Yes, something that should be amazingly easy is almost impossible.  Why?  You can drag and drop MP3 files to the Touch in iTunes, but you can’t do this with images, it just kicks out an error that it can’t be played on that device.  Bull.  In iPhoto, the Touch shows up like a camera, you can pull off but not put on.  iTunes again should be automatically doing any needed conversion in an Apple like way, but instead it just fails.  What won’t it take?  Oh, png files created by taking screenshots on a Mac for one thing…  So what do you have to do?  Create an album in iPhoto, drop things in there, then set up the syncing for that album only (lest you get everything in all your albums) for the Touch.  Far to many steps for something that should be drag and drop simple.  Once you do all that, you still can’t see the pictures in iTunes, OR iPhoto, which makes no sense.  You can only see the pictures in iPhoto that you downloaded on the Touch, not what you loaded on it.  Huh??  So there is no place to see what’s on the Touch other than the Touch, after using two applications and a lot of time getting them on there.  So much for iTunes being your place to organize your media on your Apple mobile device!
4. On the topic of Syncing, more fail.  Massive fail.  It just doesn’t work most of the time.  For one thing, before every sync it wants to back up the iPod.  You can’t skip this step.  It never explains what this is doing.  It takes FOREVER to do.  Even if it was copying the entire contents of the iPod to a backup file, it takes easily 10 times longer than the size of the data to do this.  What the hell Apple, what’s going on??  That’s also assuming it works, which over half the time it doesn’t.  After 30 minutes of backing up, it freezes and never goes further.  You wait another 30 min then cancel it.  Then try again and wait another hour and repeat until it works.  You spend all day trying to get one little app or photo on the damn iPod.  The ONLY thing you can do without pain is drop on MP3 files.  I wrote the whole blog entry waiting for a backup to run, and it’s still not done.
5. The 2.x OS was fast and stable in all ways.  3.x killed that.  Now it’s slower, less stable, and VPN is a disaster.  Since the 3.0 update VPN connections are so unreliable they are pretty much useless.  Apple has no idea why and denies any issue, yet there are many out there ranting about this.  Many have downgraded back to 2.x because it’s better to have fast and stable than have copy and paste.
6. The touch abilities of the Touch are also not all they are made out to be.  It routinely is off just enough to react with the wrong letter on the keypad so typing messages is rough.  You try to scroll and it clicks instead.  You try to move the cursor to type at a different point, good luck.
7. Download speeds are not what you see on TV.  They make it look like you can pull down an app from the store in seconds, with the iPhone, over cellular.  Bull.  Even on high speed wireless it can take several minutes to download a 10mb app that should in fact take seconds.  It’s unclear where the issue is, but given the same app over the same wireless comes down at normal speeds in iTunes on a Mac, it’s got to be an issue with the Touch.  In addition, if the normal sleep time due to inactivity kicks in, it stops the download, so you have to keep it awake while you’re waiting for it to download the app.  You can’t load another app though, since the device can only do one thing at a time, you just have to slide between app screens keeping it awake to finish the task you gave it.
8. Setting up mail… wow.  Again, it should be easy, but it’s very hard unless you’re using a simple insecure vanilla pop3 server, which even gmail and hotmail aren’t.  My home and work email certainly aren’t either.  As a result, you try to set up the Mail app, and it tries to connect before you can put in all the advanced settings you need, so it fails.  Then you try to fix it, but since it failed, it’s done.  You then find that you can’t configure what you need in the app, you need to go in to the system settings.  What?  Yep, no idea why it’s split up like that, and they don’t tell you that, and the error messages are nondescript and misleading.  Again, something that should have taken 2 minutes to set up took me half an hour.  And this again is a feature they love to talk about how cool and easy it is.

It’s to bad the Touch has all these massive issues, and I’m sure I’m forgetting something else.  If it had USB disk mode, they hadn’t pooched stability in 3.0, and the syncing wasn’t a disaster, it would still be a good IT tool and I’d recommend we get more for work.  If usability wasn’t such a disaster it would be a great device for the consumer.  As is, it’s overpriced for how broken it is.  At half the price, ok, it’s still cool for all you can do with it.  Amazingly Apple keeps selling these things by the shipload, despite all the complaints I made, which I see all over forums on Apple’s site, and they continue to not address them.  Add to that being locked in to AT&T with the iPhone, I don’t understand how they are selling these things.  I’ll take them for free, but I’ll never buy one until they fix this list of issues.  Now that the Droid is out, and the adds make it look much like an iPhone, I wonder if we’ll see a ton of apps just as cool made for that.  Could the Droid kill the iPhone?  We’ll see, someone has to give me one to play with first.