Jumping in a bit late, I wanted to comment on something I think
@Ruin Explorer said - that TSR became more "experiemental" later on. I'm not sure this is actually true. If you look at the actual product out-put of TSR during the 2E era (1989-2000), the only real difference--or at least the most marked one--is the increase in quantity, more than doubling from 1989 to its peak in 1995.
2E was, pretty much from the beginning, focused on settings. In 1989, they published products for four settings: The Forgotten Realms, Greyhawk, Dragonlance, and Spelljammer, which is about as experimental as anything that has ever been published for D&D, TSR or WotC. Then you had another quite "experimental" setting in Dark Sun added two years later.
During 2E, you have the following settings being supported to some degree (that is, having products published):
1989-00: Forgotten Realms
1989-94/98-00: Dragonlance
1989-93/98-99: Greyhawk
1989-93: Spelljammer
1990-99: Ravenloft
1990-93/95-96: Lankhmar
1991-96: Dark Sun
1992-94/98: Al-Qadim
1994-98: Planescape
1994-96: Mystara (for AD&D)*
1994: Council of Wyrms
1995-98: Birthright
1998: Jakandor
(*Obviously Mystara started as the default setting for the BECMI line, with the gazetteers published from 1987-91, but as BECMI faded in the early 90s, TSR published a series of Mystara products for AD&D).
So you have an increase in number of settings--and resulting products--from four in 1989 to eight in 92-93, then a "swapping out" of settings over the next two years, and then the contraction in 97 as things switched over to WotC.
As far as non-setting products, I don't see a huge difference. You have the "faux leather series" of books (the "Complete" options and DM equivalents) published from 1989-96, and then various accessories replacing them starting in 95. You had various box sets and miscellaneous adventures. And then, post-TSR, you have WotC's various products, like the classic module series. But these products were but a fraction of the campaign setting stuff, especially during the TSR era.
Again, the point being that I'm not sure there's a real bifurcation between a "safer" earlier period and a more "experimental" later one. It is just changing flavors, with the Forgotten Realms being the connecting setting throughout all 12 years of 2E publications.