A lot of users want to jailbreak their devices because it will let you do more with it. From a technical point of view, this is a great way to learn more about technology and having more fun. But I don't know if i'm getting old or just lazy, but I have left that crazy fun track to simply use my devices as they are meant too. Not really crazy about customization as for me, it's like playing Barby doll outfits . Just need to put my own wallpaper and i'm happy. Ok, now here's what you can do to expand your device features without doing a jailbreak... Movies: I've turned to the streaming services like Netflix and TVUplayer. Netflix has a recurring monthly fee, but in the end, it's worth that 8$ a month. No need to rip, transcode, store huge files, etc... It's available anywhere and everywhere without having to think about access, security, storage maintenance. And it's legal, you are contributing to keep a service alive. For stored movies, then I use handbrake for ripping my bought DVDs and put them on an external hardrive connected to a winxp computer, running iTunes and tversity (media server). The reason for iTunes is for my apple tv mainly. But with the new iOS 4.3, home sharing is now available on our devices making it quite handy. Since my iTunes server is a bit out of reach ( in a closet), I use Fusion Stream Store as my tversity client. I can browse all my media files, and download them on my device so I can have them on the go... Music: For stored mp3 files, I do the same as for my movies. But I actually use Shoutcast a lot as I like the diversity. I never had a big mp3 collection as I hate having to manage 1000's of files. Photos: Basically, everything is done with my iPhone 3GS as it is easier to work it than my iPad . Almost any OS can manage the pictures on a computer, so no need for big complex solutions there. It I want one of the picture on my iPad, I can use dropbox, emails, Bluetooth apps, etc... Tethering: This is probably one of the most wanted feature when doing a jailbreak. But I am lucky on that part as I can tether my iPad to my iPhone over Bluetooth. Thanks to iOS 4.3! And of course, my provider, Rogers, has enabled the feature since I have a good data plan. But in the end, you have to ask yourself if you really need that mobile connectivity on the iPad. A lot of free wifi are available everywhere, and if you have an iPhone, IT CAN DO IT! Is there a major issue that you must absolutely be able to get your email on your iPad? For sure, it's better for watching movies or online games, there's no doubt about that, but for just getting info from the web, social networking, etc, the iPhone can do it also And also, USB tethering is working with any computers... So the major issue would be provider fees for tethering. That's where doing a jailbreak could be interesting. Or simply move to another provider (lots of alternative in Canada) File storage: Yep, by doing a jailbreak, you can have full access to your file system, being able to do what ever you want. But is it that useful? There are tons of free apps that let you store files on the device itself over wifi, or USB or even Bluetooth... I really like MyMedia, oPlayerHD and Downloader. Just plain working, easy to use, and no chance of messing your device. Playing AVI, Ogg, Mkv: There was Vlc a few months ago... But seriously, it was slow... OPlayer HD Lite is a much better solution, and it lets you download files from the web... There are other player as well that can play all kinds of format for free. -------- In the end, I can do whatever I want with my iDevices without needing to jailbreak. And I avoid all the hassle of doing the maintenance and can do the upgrades as soon as they are available. So for me, doing a jailbreak only brings more customization options and a way to tether to avoid more fees (which I don't have). Last year, doing a jailbreak was interesting because you could run Skype over 3G (which was not possible at the time), have background running apps, tether over wifi since Bluetooth and USB were not working on Ubuntu. Oh one thing I do miss: having all those ringtones available without having to go thru iTunes... But, hey, is a ringtone a statement of who I am? Am I missing another key feature missing from the stock iOS ? VicoPad addict!