TL has always been troubled. Perhaps past versions haven't been as scrappy as the incoherent mess that exists today, but the land has never succeeded in presenting a palatable future than most people cared about. In a
review of TL 98 for the Washington Post writer William Booth described the newly refreshed land as, "a future that will not seem unreal because it is actually a mockup of our yesterdays, including yesterday's dreams of the future". Ouch.
All that said I don't think TL is any more popular than any other land. It has a couple of tentpole attractions and is poorly laid out, so I think it looks more popular than it actually is.