IPhone – What’s the best match iTunes version for iPhone 2G (first generation) now

Jailbreaking is the easiest way to kill the activation process, fortunately for you the 2G is cracked on such a low level is a one shot process there's a guide up on iClarified how to do it.

After that you should go have a look at which is a jailbroken firmware with a lot of the features that the iPhone 2G ended up missing out on.

It's been confirmed elsewhere that metadata alone will not give success in matching (if it were, someone would quickly find a way to just create thousands of dummy files with the right metadata). Some audio fingerprinting is going on, and you can test it by changing the metadata of one track to that of another one, and see if if matches the audio or the metadata. Still, metadata plays a role as well.

MacWorld have a note on the problem of one or a few songs not matching from an album: Basically, it seem to affect specific songs (rather than just randomly failing every n:th song). Two possible reasons for this:

1. The audio or metadata specific to that track confuses the matching algorithm (as we know, audio fingerprinting is not an exact science)
2. There is a rights issue with particular tracks that Apple haven't been able to find agreement for.