It's just a matter of supporting a video stream, really nothing impressive about it. YouTube works fine as well and also a ton of games. Getting to iOS 5 is simple, jailbreak or have something like a gen 1 iPad that can't be upgraded any further.
I've actually been chipping away at it constantly but since you haven't noticed let me put it together for you. They both have problems, and you are living in a fairy tale world if you think otherwise.
Here's just a few problems with the N64:
Hardware expansion availability
Hardware expansion pricing
Finding the software for a reasonable price (
games like Conker for 350 bucks)
Having that expensive software still prone to failure
Finding out which software requires those expansions
No ability to refund broken software
No back-ups of that now broken software
I'm a proponent of platforms that are willing to grow to move on and expand when they are young into something that will ultimately be remarkably stable just like OS X did. Apple abandoned Rosetta for a reason.