This discussion is actually borne out of a discussion in another thread—I feel like it is a topic that is valid enough to discuss, especially since in the present day, we can all agree that both have been spectacularly mismanaged.
But of Sony and Nintendo's initiatives to bring their legacy content and catalog to their modern consoles via digital distribution — PlayStation Classics and Virtual Console respectively — which one do you feel has been more mismanaged, and why? As a primer, for Virtual Console, Nintendo built up a really great catalog on the Wii, a far more diminished (but still decent) catalog on the Wii U with some enhancements to the games, barely a presence on the 3DS (even with the New 3DS exclusive SNES catalog factored in), and so far, the Virtual Console is missing entirely in action on Switch, and we have no indication that it is actually coming to the system.
For PlayStation Classics, Sony had a great catalog of PS1 games that was available across PSP and PS3 (with Cross Buy too, all the way back in 2008!), and a handful of PS2 games (available only on PS3). On the Vita, there were no PS2 games available, and multiple PS1 games were caught in rights limbo, either unavailable on the system at all, or only available via a PS3->PSV transfer. On PS4, there are no PS1 games available whatsoever (making it the only PlayStation console that can't play PS1 games, in fact), and some PS2 games available with some enhancements, and that's it.
Which of the two do you think has been handled worse, and why?
A NOTE ABOUT XBOX:
While we are on this topic, I do want to give a shout out to Xbox—they have the smallest legacy coatalog of the three platforms (this is not a quality related judgement, just a recognition that Xbox is the "youngest" console family of the three), but they are most determined to maintain it. Great backward compatibility features on Xbox One that enhance Xbox and Xbox 360 games, games from every single Xbox console represented on the console, and digital continuity (so you don't have to repurchase content! Something neither Sony nor Nintendo has consistently managed) makes their showing in this area flat out the best of the lot in my opinion. Sony and Nintendo could stand to learn from Microsoft.