First, for the "I'm never planning on leaving AT&T, so why would I unlock?" crowd, two things: first, resale value; and second, international travel. Your phone is worth more on the second-hand market if it is unlockable (whether "factory-unlocked" or hack-unlocked), and if you travel around, it is nice to have the freedom to be able to stick in a prepaid, international SIM in whatever country you happen to be in at the time, instead of paying AT&T out the nose for their BS international roaming rates (especially data...).
However, there is another whole side to purchasing a factory-unlocked iPhone internationally that hasn't been explored in this thread. If I had the option of buying a factory-unlocked phone domestically instead of an AT&T-locked one and then suffering through software unlocks, yeah, I'd do it in a heartbeat, even if I had to pay full-price for the handset. But because my only option to getting a factory-unlocked iPhone is by purchasing overseas, "no thank you."
Why? One word: warranty.
I agree that it is an ****** move by Apple, but it is still the case that unlike nearly every other product that Apple sells, warranty coverage on iPhone is NOT INTERNATIONAL. It is, in fact, limited to the country within which it was purchased. So to get it serviced in the event that it needs it, you either have to travel back to that country yourself, or send it to a friend in the area (if you have one). If you took that expensive, factory-unlocked phone into a US Apple Store for service, they would refuse you at the door (and even if they didn't have that policy, they couldn't replace it for you with anything other than an AT&T-locked one anyway, which would still necessitate that you get your phone serviced overseas if you wanted to keep it factory-unlocked).
I hate, hate, hate phone subsidies and BS SIM locks, but because 95% of my phone use is within my own country, it would be more inconvenient for me to not be able to get the phone serviced or replaced locally than it would be for me to have a hacked-unlock and risk losing the unlock because my phone needed service.
Not to mention, what do you do if you are phone-shopping for an internationally-unlocked model, and the very first one you get out of the gate is DOA or defective in some other way, and you only discover that once you get back over the border into your own country? I had a terrible experience with both my 3G and 3GS phones (the iPhone 4, in contrast, has been awesome...very reliably-built hardware that has given me 0 troubles so far!), and both required warranty replacement service twice within their lifetime (the 3GS required it twice within the first two weeks of ownership). I can't even imagine having to go through the hassle of getting that taken care of without a domestically-recognized warranty. With the 3G and 3GS, since I had AppleCare on them, it was literally call Apple, talk to them for 5-10 minutes, and wait for FedEx to show up the next day with a new phone and a prepaid box for me to send back the defective one with. I didn't even have to take time out of my day to go anywhere...they came to me!
Again, I'm not arguing that for some people, it might not make sense to go factory-unlocked instead of screwing around with software hacks. Maybe you visit the country you bought it from on a routine basis, so it's not an inconvenience to you if you do need to get your phone serviced. And I'm also not arguing that phones shouldn't be unlocked from the get-go, or that Apple is justified in denying warranty service to phones purchased elsewhere (totally BS, Apple; I mean, seriously!). I'm just saying that given the way things are, for a lot of people, it would be a huge inconvenience to deal with warranty claims, and this huge inconvenience can overshadow the benefits of a factory unlock.
Finally, I want to address jailbreaking for a second. You sound like you only jailbreak in order to unlock, which is why you lump waiting around for jailbreaks AND unlocks together. Most of us who jailbreak, however, don't simply do it for the unlock. (In fact, since I have yet to travel outside of my country with my iPhone 4, I haven't even bothered to install the unlock yet, but I was still jailbroken from day 1!) Oftentimes, the jailbreak and the unlock are worked on and released on completely different timetables with respect to one another, so just because a phone model has been jailbroken doesn't even mean it has been unlocked yet.
Now, if I was lucky enough to own a factory-unlocked iPhone, I still wouldn't jump immediately onto the upgrade bandwagon whenever a new Apple firmware came out, whereas it sounds like you would. To paraphrase YOU, it's in your best interest to THINK about what you do before you just go ahead and blindly do it. Right? And in the case of software upgrades from Apple, I would urge you to stop and think before you blindly jump in and upgrade your phone before a jailbreak is available. (And I hope that even if you do decide to upgrade that you are still aware enough to be backing up and collecting the SHSH bundles for your phone for each firmware version released by Apple. Because not being able to downgrade is COMPLETE BS. Just like having your baseband locked to a particular carrier's SIM is complete BS. Right?)
Even if you don't use the jailbreak for anything yourself, just like unlocked and unlockable phone are worth more second-hand, jailbroken and jailbreakABLE phones are ALSO worth more. Whenever Apple comes out with a new software release that a jailbreak is not available for yet, phones released from the factory with that software on it are worth less than phones that have not yet been loaded with the software, or which have it but also have backup SHSHs for older versions. (There have even been times, because of the way certain jailbreaks work, where if you had a phone that was still of the most current generation but purchased a few months ago, if you paid attention and made good decisions about software upgrades, you could actually run the newest software on it AND be jailbroken, but that same model phone purchased in the store that very day with the latest software on it would NOT be jailbreakable.)
Personally, in my mind, the war against jailbreaking that Apple is fighting is a much more important war for us as consumers to win than the battle against SIM locks. Apple is only fighting the SIM lock war because they are victims (willing victims, admittedly, but still victims nonetheless) of the cellular phone industry juggernaut. SIM locking was fashionable WAY before Apple entered the game, and if they wanted to play the game, they had to play by their rules. If Apple could get away with selling unlocked phones in the US right now, they would.
However, Apple has demonstrated that the software "jails" they have erected are something they are very much in favor of. They are trying to curate the user's experience through those jails, claiming that they are needed for the benefit of the user for security, or for software stability, or for UI consistency, or whatever. But the freedoms they are stealing away from consumers with these artificial software limitations are very much analogous to the freedoms of choice that SIM locks also take away from consumers, just in a different area.
The difference between the two is that one was invented by and is championed by Apple, and the other was not and is not. For the one that wasn't -- SIM locking -- the battle needs to be fought on different ground for it to be effective, because the enemy in that battle happens to be somebody other than Apple. For the issue that is championed by Apple -- software jails -- you need to be no less of a thinking, alert, and aware consumer than you do with the SIM locking issue.
-- Nathan
However, there is another whole side to purchasing a factory-unlocked iPhone internationally that hasn't been explored in this thread. If I had the option of buying a factory-unlocked phone domestically instead of an AT&T-locked one and then suffering through software unlocks, yeah, I'd do it in a heartbeat, even if I had to pay full-price for the handset. But because my only option to getting a factory-unlocked iPhone is by purchasing overseas, "no thank you."
Why? One word: warranty.
I agree that it is an ****** move by Apple, but it is still the case that unlike nearly every other product that Apple sells, warranty coverage on iPhone is NOT INTERNATIONAL. It is, in fact, limited to the country within which it was purchased. So to get it serviced in the event that it needs it, you either have to travel back to that country yourself, or send it to a friend in the area (if you have one). If you took that expensive, factory-unlocked phone into a US Apple Store for service, they would refuse you at the door (and even if they didn't have that policy, they couldn't replace it for you with anything other than an AT&T-locked one anyway, which would still necessitate that you get your phone serviced overseas if you wanted to keep it factory-unlocked).
I hate, hate, hate phone subsidies and BS SIM locks, but because 95% of my phone use is within my own country, it would be more inconvenient for me to not be able to get the phone serviced or replaced locally than it would be for me to have a hacked-unlock and risk losing the unlock because my phone needed service.
Not to mention, what do you do if you are phone-shopping for an internationally-unlocked model, and the very first one you get out of the gate is DOA or defective in some other way, and you only discover that once you get back over the border into your own country? I had a terrible experience with both my 3G and 3GS phones (the iPhone 4, in contrast, has been awesome...very reliably-built hardware that has given me 0 troubles so far!), and both required warranty replacement service twice within their lifetime (the 3GS required it twice within the first two weeks of ownership). I can't even imagine having to go through the hassle of getting that taken care of without a domestically-recognized warranty. With the 3G and 3GS, since I had AppleCare on them, it was literally call Apple, talk to them for 5-10 minutes, and wait for FedEx to show up the next day with a new phone and a prepaid box for me to send back the defective one with. I didn't even have to take time out of my day to go anywhere...they came to me!
Again, I'm not arguing that for some people, it might not make sense to go factory-unlocked instead of screwing around with software hacks. Maybe you visit the country you bought it from on a routine basis, so it's not an inconvenience to you if you do need to get your phone serviced. And I'm also not arguing that phones shouldn't be unlocked from the get-go, or that Apple is justified in denying warranty service to phones purchased elsewhere (totally BS, Apple; I mean, seriously!). I'm just saying that given the way things are, for a lot of people, it would be a huge inconvenience to deal with warranty claims, and this huge inconvenience can overshadow the benefits of a factory unlock.
Finally, I want to address jailbreaking for a second. You sound like you only jailbreak in order to unlock, which is why you lump waiting around for jailbreaks AND unlocks together. Most of us who jailbreak, however, don't simply do it for the unlock. (In fact, since I have yet to travel outside of my country with my iPhone 4, I haven't even bothered to install the unlock yet, but I was still jailbroken from day 1!) Oftentimes, the jailbreak and the unlock are worked on and released on completely different timetables with respect to one another, so just because a phone model has been jailbroken doesn't even mean it has been unlocked yet.
Now, if I was lucky enough to own a factory-unlocked iPhone, I still wouldn't jump immediately onto the upgrade bandwagon whenever a new Apple firmware came out, whereas it sounds like you would. To paraphrase YOU, it's in your best interest to THINK about what you do before you just go ahead and blindly do it. Right? And in the case of software upgrades from Apple, I would urge you to stop and think before you blindly jump in and upgrade your phone before a jailbreak is available. (And I hope that even if you do decide to upgrade that you are still aware enough to be backing up and collecting the SHSH bundles for your phone for each firmware version released by Apple. Because not being able to downgrade is COMPLETE BS. Just like having your baseband locked to a particular carrier's SIM is complete BS. Right?)
Even if you don't use the jailbreak for anything yourself, just like unlocked and unlockable phone are worth more second-hand, jailbroken and jailbreakABLE phones are ALSO worth more. Whenever Apple comes out with a new software release that a jailbreak is not available for yet, phones released from the factory with that software on it are worth less than phones that have not yet been loaded with the software, or which have it but also have backup SHSHs for older versions. (There have even been times, because of the way certain jailbreaks work, where if you had a phone that was still of the most current generation but purchased a few months ago, if you paid attention and made good decisions about software upgrades, you could actually run the newest software on it AND be jailbroken, but that same model phone purchased in the store that very day with the latest software on it would NOT be jailbreakable.)
Personally, in my mind, the war against jailbreaking that Apple is fighting is a much more important war for us as consumers to win than the battle against SIM locks. Apple is only fighting the SIM lock war because they are victims (willing victims, admittedly, but still victims nonetheless) of the cellular phone industry juggernaut. SIM locking was fashionable WAY before Apple entered the game, and if they wanted to play the game, they had to play by their rules. If Apple could get away with selling unlocked phones in the US right now, they would.
However, Apple has demonstrated that the software "jails" they have erected are something they are very much in favor of. They are trying to curate the user's experience through those jails, claiming that they are needed for the benefit of the user for security, or for software stability, or for UI consistency, or whatever. But the freedoms they are stealing away from consumers with these artificial software limitations are very much analogous to the freedoms of choice that SIM locks also take away from consumers, just in a different area.
The difference between the two is that one was invented by and is championed by Apple, and the other was not and is not. For the one that wasn't -- SIM locking -- the battle needs to be fought on different ground for it to be effective, because the enemy in that battle happens to be somebody other than Apple. For the issue that is championed by Apple -- software jails -- you need to be no less of a thinking, alert, and aware consumer than you do with the SIM locking issue.
-- Nathan