At iOS5 the only jailbreak available is a tethered jailbreak. That means it has to be connected every time you turn it on or it locks at the boot logo.
This isn't inconvenient if you never turn your phone off, and it plugs into the charger every night, which I do.
The technical knowhow required to jailbreak the phone and unlock is a moderate level, if you can follow instructions, and google things yourself, you should have no problem. Mind you, if you get nervous easily around poorly produced sites, or are inexperienced in dealing with "basement dev" software as I like to call it, you might feel like this whole process is a little scary. None of the software you use, or websites you will go to look very flashy or well polished, but they all work very well, they have a purpose of getting the job done and nothing else. (Also everything is free. If they ask you for money you're getting scammed, its a bad site, go back and try again somewhere else).
After it is jailbroken and unlocked there is nothing else special about using the phone and it'll be the same user experience (plus jailbreak goodies if she uses them).
Also to be considered, an untethered jailbreak WILL come out eventually for iOS5.0 and you will be able to update the jailbreak (simply by 're-jailbreaking' with the new jailbreak software), and your iphone will be untethered, meaning you can start it up without the PC.
However, if your phone's baseband (Settings > General > About > "Modem Firmware") is 05.14.02 or any higher sequence, you will have to "upgrade" to the ipad baseband, 06.15.00 (redsn0w can also do this for you, its as easy as jailbreaking is).
Only problem with upgrading the baseband, is that you run the risk of losing GPS function, you lose Apple guaruntees, and they will know you've unlocked your phone and jailbroken it. It is irreversible at this time and there is little to no hope of that changing.
And if you do update to the 06.15.00 baseband, you can never run stock firmware. I.E. you cannot update your phone via iTunes or restore your phone or anything to an original apple iOS version. You can ONLY run jailbreak firmwares.
This doesn't mean you can never update your phone, but it does mean you must wait until a jailbreak comes out for any new iOS versions, before you can update your iPhone to the new jailbreak version. In which case you should come back to the forums for special instructions on how to do so, if you don't know.
If your baseband is unlockable however, you have MUCH less to worry about, and unlocking is a lot safer and more risk-free.
From what it sounds like, the tethered jailbreak is your biggest issue, which makes sense, most people don't like dealing with that. The whole jailbreak + unlock process took ME about 3-4 hours, including research time, time to download all the things I needed, and the actual physical process of doing everything.
ALSO!!! AFTER ACTION REPORT!!!
I got my iPhone successfully updated to 06.15.00 last night, unlocked it via ultrasn0w, corrected the activation via SAM (optional, improves battery life among other things), and after my gps stopped working! I was only testing the gps through wifi however.
But this morning, I went and got a bell sim, popped it in and switched my account over from my CDMA phone to my new iPhone, and I got it working INSTANTLY with no hassle. The unlock worked amazingly
And I checked after putting in the SIM and MY FREAKING GPS WORKED AGAIN!!!! GIRLFRIEND!
The end.
/endrant
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