I understand that licensing negotiation is a major factor, but I don't think that the requirement to "add trophies" should be dismissed.
Not dismissing it - but we have over a decade of signs pointing to the fact that licensing is the biggest bottleneck across 3 different platform holders (eg. see above).
I know you pointed out Microsoft's efforts to address forward-looking licensing during the Xbox 360's market tenure. Apparently Sony has not learned this lesson, as it is an
ongoing problem for them to this very day.
Just a few weeks ago, Suikoden IV was released as a PS2 classic...but only for PS3. It's not available on PS4. There must be some reason why Konami stonewalled on a PS4 version. It wouldn't surprise me if the requirement to add trophies is an unwanted burden here.
Regardless of Sony's prior mistakes in handling PS2 classics for both PS3 and PS4, wouldn't
right now be the best time for them to start mending the holes in their policies? Start releasing new PS2 games simultaneously on both systems. Make this a requirement for any new PS2 classic from this point forward. Mandate that publishers are on board with this,
and mandate cross-buy for all new PS2 classic games.
Once they've established the new standard, go back to previously released PS2 classics, and start instituting the policies on those games as well. Allow anyone who previously bought a PS2 classic on either PS3 or PS4 to do a cross-buy carryover, and have access to the same game on
both systems.
That is how you put smiles on your customers' faces, and retain and reinforce their loyalty.