I subscribe to a service called PrimeCuts. It's a service that gets music in the hands of mobile DJs and radio stations, with the full blessing of the RIAA (not that I necessarily desire to be in the RIAA's good graces, but if the Tannenbaum and Thomas-Rasett cases prove anything, it's that they aren't fair regarding noncommercial infringement, thus, commercial infringement in the context of being a mobile DJ would involve that much less fairness...). I cannot (legally) sell the CDs they send me on eBay. I'm pretty sure I can't even legally give them away, for free, even as a permanent transfer. My only recourse, should I wish to absolve myself of the CDs, is to sell my DJ business. The discs are a business asset and they can be permanently transferred as a part of the whole business being transferred, but not as discs by themselves. I think that there is merit to some sort of parallel in this case.
Usual not-a-lawyer disclaimers apply, but my logical reasoning says that a permanent transfer of the iTunes account would allow for digital content to be used by the beneficiary of the will. The apps/music/videos are still tied to the same iTunes account and aren't being transferred between accounts (a requirement for your 'secondary market' analogy to apply), but the account is being used by the beneficiary of the will. Now, for this to work, there needs to be a few things determined:
1.) is digital content given to an account, or a human?
1a.) If account, is it a reasonable argument that since the iPad was left, that the account is an inexorable part of the device? e.g. if a house is stated in a will, but the keys are not, is the beneficiary thus not allowed to enter the house?
1b.) If human, does the Apple EULA explicitly state that the rights cannot be transferred within a will? If so, it seems grounds for a court battle, since intellectual property is transferred all the time as a part of a will - art, vinyl records, DVDs, computer software on plastic disc, etc. Is there sufficient legal precedent to state that content purchased from Apple is not subject to the same laws that allow DVDs to be subject to the terms of the will?
2.) Could it be argued that the only reason this case exists is because there is a passcode on the device, without which, Apple probably wouldn't have been contacted in the first place?
3.) It is entirely possible that there are notes, voice memos, photos, and videos that were generated by the deceased, not by Apple or its licensors. Apple's withholding of the passcode prevents the user from accessing that data, which seems like shaky ground as well.
Then again, this is the problem with 'magic boxes' - people don't quite understand exactly how things interrelate, which means that things that aren't explicitly specified are subject to ambiguity for no reason.