Why waste energy and ressources on doing these remakes of products that are almost new ? Why ? So many old school modules lying around that beg to get a conversion to 5E! Tyranny of Dragons and then this are two exemples of wasted time and efforts. My opinion, of course.
Because they've done a ton of them en masse in Tales from the Yawning Portal, three more of them in Ghosts of Saltmarsh and then have licensed an unknown quantity of them to Goodman Games, which is republishing them as part of their Original Adventures Reincarnated line.
Between all of those, there really
aren't a ton of great classic adventures still sitting on the shelf. We're getting Castle Amber and Temple of Elemental Evil from Goodman Games in the next year, and I would bet big money on Palace of the Silver Princess at some point.
I think it's pretty likely we'll see Desert of Desolation get the Ghosts of Saltmarsh treatment some time in the next few years. I suspect the Slavers series is being considered for the same, although with the ethnic stereotypes of some of the slave lords either replaced or modernized.
Given all the stuff with Gail Gygax, I don't think we're likely to see anything that touches on Castle Greyhawk too closely, which would rule out even Dungeonland and the Land Beyond the Magic Mirror.
Dragonlance, for whatever reason, is something WotC wants to leave on the shelf, after clearly having thought about doing something with it during the 5E playtesting phase, when kender were a halfling subrace.
Once you've gone through that big whack of content, what's left that has a really big mass audience? The 2E stuff famously had a deeply fragmented audience, meaning even the most popular Forgotten Realms, Dark Sun, Ravenloft or Planescape stuff has a much smaller installed base of nostalgic fans than the 1E stuff does. (And that's to say nothing of Spelljammer, Maztika, Al-Qadim -- which I loved, for the record -- Jakandor or the historical booklets.)
Also, with the pandemic currently looking like it's going to be lasting quite a while, especially here in the US, republishing their most popular and most critically successful campaign requires a lot less work than making something from scratch (note that all of this content is previously existing, and just repackaged and enhanced) and is likely to be a big hit with all the new and semi-new players at home this October, just in time for a second wave of COVID-19 keeping people indoors.
If you can't go trick or treating in your neighborhood this year, why not go knock on the door of Castle Ravenloft?
