I have my 3G iPhone jail broken and using T-Mobile instead of AT&T. I pay approx. 30 bucks for 500 minutes including nights and weekends and an Edge internet data plan. Its not fast, but its functional and cheap. Just what I needed for my first cellphone. Yes, I'm 34 and this is my first cell phone. I tried to avoid cell phones as long as I could, but finally gave in
. As far as cons, I can't think of any. If you're jailbreaking and going to something like T-Mobile, the biggest con I can think of is the lack of 3G availability... other than that, and especially since you're planning on jailbreaking an iPod, its only pros.
I have a jailbroken iPod touch which I use for everything. The cons are that when new firmware is released, if you sync with iTunes, you lose everything basically. There are ways around it, but it is annoying to say the least. Pros: multi-tasking, themes, more competition (though much of it is more expensive).
Would I go back to non-Jailbreaked iPod touch? Yes, I find that both systems work very well and are just different sides to the same coin. Don't ask about anything illegal as I don't participate in any of it.
Background apps
Use 3G as Wifi
Emulators
Dl'ing off of youtube
Playing flash videos
Lots of productivity things that apple doesn't yet allow, such as sms counters
transferring files like onto a usb device
custom themes
using Wi-fi restricted apps over 3g, great for voip
and...*cough*free apps*cough* >_>
Cons:
Possible slowdown from always-on apps, such as the themes. Those would be your major hits. I don't use them due to that. Others shouldn't be a problem
For the upgrading, if you chose Rock Apps in addition to Cydia, you can store all your installed packages there. I've tried it before and it works great
Jailbreaking has become far more beneficial now, especially if you have an iPhone as opposed to an iPod touch.
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