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I use Facetime to talk to my wife when I'm out on the road occasionally for work. Basically a video to video chat. Works pretty well.
Jailbraking an apple device is basically turning it from a read only device to a read/write device. It allows you to download different programing codes and upload them yourself so it's more customizable. For example it will allow you to modify things you wouldn't be able to modify on a stock ipod/iphone. On my jail broken Iphone 4s I can add more rows customize backgrounds, change the way the phone works basically. That is a basic overview of jailbraking. There is tooonss of stuff you can do once jailbroken. Here is a link to iphoneforums.net about jailbraking and another for the different applications: http://www.iphoneforums.net/forum/iphone-jailbreaking-17/, http://www.iphoneforums.net/forum/jailbreak-applications-tweaks-70/. (works basically the same way for an Ipod touch/iPad/and other apple idevices) Those go in-depth on the different things you can do once jailbroken. I have a customized boot screen, lock screen, with custom backgrounds and changes the way the icons look. It takes a little of getting used to, by that I mean how to utilize it once jailbroken, but once you do it, there's no looking back lol. It will work just the same either way, jailbreak just makes it better.
be careful though i heard jailbreaking an ipod voids any warranty that you have on the product. since apple dosent really approve of changing their codes.
Facetime only works with other Apple products tho. Maybe check out Skype, its a free app and a free service. I like it. I use it with my sister and my mom
You can buy phone service through skype but as for just the video chat stuff, its all free. I downloaded the app for my iTouch for free
Technically it does "void" your warrenty, but if anything ever happens to you phone/ipod, all you have to do is hook it up to your computer do a reset and you'll be good to go. There will be no trace of a jailbreak ever occuring on your phone/ipod. I pay for added insurance anyway so I don't care about factory warrenties through Apple. They make too much money as it is. I understand what you mean, I thought it would be too complicated for me, but they've made it so simple now. It used to be you had to hardwire and "re-program" your iphone/ipod by setting it into a default programming mode that was hard to master until you had the right sequence down, but now it's plug in, hit the jailbreak button, wait 2-5 minutes, and then enjoy! lol
