We love jailbreaking our iPhones, iPod touches, and iPads because it opens up it opens up so many great new possibilities. It also has the potential to cause a lot of problems and headaches. Here's why you might not want to jailbreak.
Goodbye Stability and Safety
While jailbreaking can provide you with plenty of options to increase the functionality of your iDevice, it can also cause things to work unexpectedly. Little extensions and add-ons can cause applications to crash, and you're left to figure out what's causing the problem yourself. Jailbreaking turns your mobile into a regular computer in the sense that solving a problem is no longer simple — it requires some knowledge and effort (if not a lot of it) to fix a problem. Yes, there are tools to help you troubleshoot problems but it's not like it's something that's easy or you're always going to want to do. If you like to know that things are just going to work, jailbreaking may not be your best bet.
Additionally, some security experts believe that jailbreaking your iDevice isn't safe from a security standpoint. Opening up your device to new possibilities can also mean opening up your device to new vulnerabilities. While you can take steps to prevent that, it, again, takes a bit of effort that you may not be willing to perform.
You Don't Get to Update iOS as Soon or as Easily
Updating a jailbroken device sucks. When you update, you lose your jailbreak, need to re-jailbreak, and then re-install all your jailbroken apps and extensions. There are tools like PkgBackup that can make restoring that stuff a bit easier, but it's still not the same as performing an actual OS update. This can be frustrating and may prevent you from regularly updating iOS. In some cases this is fine, but given Apple's latest track record there have been some significant issues requiring many incremental iOS updates (such as the location tracking "bug") and those may be pretty important to you. (Of course there are generally jailbreak fixes for these things, such as Untrackerd — which fixed the location tracking bug.) When you're jailbroken you have to wait a bit longer to update if you want to continue jailbreaking your device. This can be really frustrating when there's a big software update with lots of neat new features or if you really need the latest bug fix. If you're going to jailbreak, you better be patient.
You'll Be Restoring Often
Jailbreaking is fairly easy to do — when it works. Sometimes, for unexplainable reasons, jailbreaking just fails. Either you'll have to keep repeating the process until it works, which gets annoying, or you'll find yourself performing a full restore pretty often. While restoring iOS doesn't take all that long, restoring all your music, photos, videos, and other media isn't a fast process. When you're jailbreaking, you should plan to lose up to four hours of your time in case of a problem. This isn't something that always happens, and hasn't happened to me at all this year, but it has happened before and has happened to a lot of readers (because I hear from them). It can suck, so if you're not prepared to put in the time — even though you may not have to — you shouldn't jailbreak.
Good Jailbreak Apps are Pricey
If you don't like paying for apps on the iTunes App Store, you're going to hate paying for them on the Cydia Store. There are some amazing apps, and, personally, I have no problem shelling out the money for the developers, but the best ones are often paid apps/extensions and cost more, on average, than what you'll find on iTunes. If you're not ready to shell out some cash for some of the best options — like better notifications, better SMS, better app switching, retro game emulation, and more — you might want to keep your iDevice in its unjailbroken state.
All of this said, I still prefer to jailbreak my iDevice. I think it's worth the inconvenience and I don't care much about new updates now that iOS is pretty well-rounded. But I'm definitely not the majority in that case. Jailbreaking is not for everyone, so it's good to know the downsides before you jump in.