I’ve been through many generations of iPod, from my first U2 Special Edition 4 years ago to the 2nd Gen iPod Touch earlier this year. I love my new iPhone 3GS, but there are just a few things that annoy me and I hope Apple is listening. Here we go…

1. iTunes Sync - It’s a double-edged sword. It works great for contacts, calendars, and especially iTunes content. But why can’t we allow 3rd party developers to join the fun? While my “core services” are synced beautifully either OTA (via MobileMe) or every time I dock, the rest of my apps are stuck in the past. They languish in the dark corners of my iPhone, their data getting stale, awaiting a time when I can remember to sync them. Apps like DocsToGo, Appigo’s ToDo, SplashID, and DVDPedia have all been forced to develop their own Wi-Fi based sync mechanisms. Some of them are launched from the iPhone, some are launched from the desktop, but all of them require opening the apps on both sides and starting that handshake. Shame on Apple for allowing this wild non-uniform monstrosity to occur… Please let it be opened up in the next version of iTunes and we can just put this chapter behind us.

2. iCal Invitations - This was promised to us prior to the release of iPhone 3.0 and then mysteriously pulled, well, sort of. The ability to invite others or accept a calendar item is key. This is especially true for busy families who want to share specific calendar entries with each other, not entire calendars. The weird thing is that they actually have this functionality, but it’s only enabled when you’re connected to an Exchange server. I sometimes dream about how easy it would be to just turn it on for everyone, just like it is in… what was it? Oh yeah, iCal on the Mac… Please Apple, it’s not just for business users.

3. SMS - I won’t point out the obvious lack of MMS, as that’s clearly an AT&T problem. The SMS app has some other glaring ommissions I’d like to highlight here. For starters, why can’t I customize the color or layout of the chat screen. I don’t really like the cartoony bubbles that Apple has decided is best for me. Also, why can’t I opt to see a timestamp on each message, not just at the “start of conversation”. And the worst offender is, there is no auto-resend. If I send a message and I’m out of coverage, it fails and waits for me to re-send. Most phones I’ve used would resend when the phone is back in range. If you’re a heavy texter and your commute takes you through some tunnels, this can be a real annoyance.

4. Battery Life - 3-4 Hours. That’s what I get when I’m actually using my phone for apps. I can burn (poor choice of words?) the battery all the way down to 65% on my way in to work, and that’s only 90 minutes. It’s for this reason that I keep my phone charged at home, charged at work, charged in the car, and I carry a cheap knock-off iPhone battery pack in my bag. If I ever find myself away from an outlet for more than a few hours I better start conserving. Should I really be thinking about my battery this much? Hopefully some advancements can be made from the software side to improve the battery conservation.

5. Bluetooth stability - My car and my iPhone just aren’t getting along. My Audi has this annoying piercing chime on every hands-free connect and disconnect. So, I’m painfully aware that every once in a while the iPhone drops the connection and re-establishes it 10 seconds later. I can’t find a reason for this. Is it the placement of the phone? Speed of the car? The weather outside? I have no idea. This hasn’t happened during a call yet, but I’m sure it will. It’s just waiting for a really important call. This has never affected my other phones.

6. Bluetooth A2DP - When Apple said they were supporting A2DP in their latest revision of the software, I was ecstatic. I have my favorite Motorola S9 headphones which have been gathering dust since my Palm Centro days. But wait, something isn’t right. You see, Apple hasn’t implemented A2DP in full form. They did it without the AVRCP protocol which in laymans terms, prevents these fancy headsets from controlling the track forward/backward and Play/Pause. But it gets worse! You can’t watch any video content over the A2DP protocol because the extra processing required to send the audio over bluetooth lags behind the video. Let’s hope they had time to focus on patching this one for the next release. It’s just easier to say the iPhone can’t do A2DP just yet…

7. Music Video Support - I enjoy mixing in some music videos to my iPhones music library. It’s a nice treat to get treated to a video when playing on shuffle. The problem here is that these music videos are being mishandled. They are being treated like any other video content, in that they resume playback from a paused point. Music videos should always start from the beginning. I know I have my files tagged properly and there is a setting on the iPod for “Resume Video from Paued Point” but this setting should not apply to Music Videos.

8. Video Podcasts - I don’t want to watch my video podcasts. Does that sound crazy? If you’re Apple, maybe so. It is just way too cumbersome to play them in audio only mode in the background. Once you exit the iPod application, the video stops (unlike music, which always continues playing). The only way to achieve this, it to start the video, leave the iPod, and then click the Play/Pause button on your headphones. What if you’re using headphones without a button or mic? You’re SOL. What they need to do here, is allow the shortcut double-tap, which I’ve set to iPod, to open only the iPod controls, even if the iPod isn’t playing, or allow the video to play after you exit. Annoying!!

9. Multitasking - I know, this is a big one and I thought I would be OK without it. But now it’s come to haunt me. Most games and apps do “remember” where you were when you leave them, so that works fine. But for a true background app, it just won’t work. The most obvious case of this is with Pandora and Sirius. You can enjoy these music services all you want, as long as it’s the ONLY thing you do. That’s right, you can’t simply “home key” out of Sirius and let the music play. It’s for this reason that I rarely use these apps. Such a shame… They should be treated the same way the iPod app is, and allowed to play freely in the background of the OS.

10. No Doubletime Video - One of the nifty new features of OS 3.0 is the adjustment of audio speed playback. I can take my podcast down to 1/2 speed or double it at 2x speed. This is not the way I’d want to listen to an every podcast, but when I just want to finish a clip or wrap up a long, drawn out MacBreak Weekly, i just hit the 2x button. I can still understand it and it saves time. Why can’t we do this for Video podcasts as well??

Bonus - One more item of note on Music Videos. Sometimes I feel like I’m the only one doing wierd things like this, so I wont count it against them, but I do think it’s a bug and should be addressed. I dock my iPhone horizontally, both at work and in the car. When my randomized music collection hits a music video it plays great, but when the video ends, the iPod turns from the default “cover-flow” view to the vertical view. The only way to “reset” this is to flip vertically and back to cover-flow only horizontal. Why? I don’t know, but it annoys me…