Jakandor is actually the kind of thing they might be able to do today too. It was always envisioned as a limited thing: one island, about the size of Great Britain IIRC, with two rival human cultures and pretty much no other sapients. A total of three books (which would probably be one today): one for each side and one with some common things and a bunch of adventure/campaign ideas. Done.I never bought Jakandor.
The problem was trying to support multiple full-fledged campaign settings at once: Forgotten Realms, Greyhawk, Birthright, Planescape, Dark Sun, Mystara, Dragonlance, Al-Qadim, Spelljammer, Ravenloft, etc. (I think some of those probably didn't overlap, but still). And we're talking heavy support. Birthright had like 25 things released in two years (1995 and 1996) – sure, a lot of those were short "Player's Secrets of X", but it also included five boxed sets!
I thought the Random House thing was primarily about the novels?These are really the same issue.
Overall, TSR was losing money on RPG sales. That doesn't mean every book was unprofitable - the core books were still probably making money even in the lean years. But they were publishing a ton of other books that were losing money, and that business model basically developed because of the Random House deal.