To Jailbreak or not?

Advantages? Access to more apps, Theme changing, more user friendly...

Disadvantages? Haven't found a single one in 2 years.

Jailbreaking installs Cydia, the "App Store" for jailbreakers.

 
There are unlimited advantages, and absolutely zero disadvantages. I've got a jailbroken 3GS as well, along with a jailbroken Touch.

Jailbreaking it installs Cydia, and when you open Cydia for the first time it downloads and installs various things you'll need. One of the apps it installs is "Installous". That's where you go to get apps, and it uses various filesharing sites for the downloads(mainly fileape, filedude, mediafire, and megaupload). Cydia's "apps" aren't actually apps. You download themes, tweaks, and cheats/hacks from Cydia. There are apps, but they're not the ones you can get from the App Store. And yes, you can still use the App Store. Installous actually doesn't have apps that you can download for free on the App Store, so you have to use it occasionally.

DON'T EVER UPDATE ON THE APP STORE. Also, make sure your version of iTunes won't ruin your newly jailbroken phone.

Also, jailbreaking should be an easy process lasting no longer than two minutes or so for the whole process.

 
Only downside iirc is you have to be using iOS 3, once you use iOS 4 you can't jailbreak. Unless they fixed it
They did. I'm pretty sure even the latest firmware is able to be jailbroken. I'm on 4.2.1 right now, and have had that since I jailbroke the phone, but I know you can jailbreak even newer versions.

 
There are unlimited advantages, and absolutely zero disadvantages. I've got a jailbroken 3GS as well, along with a jailbroken Touch.
Jailbreaking it installs Cydia, and when you open Cydia for the first time it downloads and installs various things you'll need. One of the apps it installs is "Installous". That's where you go to get apps, and it uses various filesharing sites for the downloads(mainly fileape, filedude, mediafire, and megaupload). Cydia's "apps" aren't actually apps. You download themes, tweaks, and cheats/hacks from Cydia. There are apps, but they're not the ones you can get from the App Store. And yes, you can still use the App Store. Installous actually doesn't have apps that you can download for free on the App Store, so you have to use it occasionally.

DON'T EVER UPDATE ON THE APP STORE. Also, make sure your version of iTunes won't ruin your newly jailbroken phone.

Also, jailbreaking should be an easy process lasting no longer than two minutes or so for the whole process.
How would I go about making sure my version of itunes wont ruin things?

 
Well, 10.4.1(you can check the version by going to Help -> About iTunes) is jailbreak safe and I think it's the newest version. I just know that certain specific updates weren't jailbreak safe for whatever reason.

 
Yes. And if for some reason it chooses not to, there are alternative ways available for jailbroken iDevices.

I sync mine all the time, and it syncs all of your apps from Installous as well.

 
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