So, on to the listening results. Overall, the 1950s songs vary as far as whether they are better presented on the anniversary disc or the older releases, while the 1980s songs are better on the older releases. If this doesn't make sense, I'll try to explain what's happening here, at least according to my ears. The main reason that many of the "oldies" sound worse is the use of inferior masters for the transfers. Some of them sound either thin ("Hey Baby") or muddy ("In the Still of the Nite"), while on the anniversary disc, all of them sound comparatively full, clean, and clear (making allowances made for the varying fidelity of the original recordings). That being said, even here things can vary a bit - I prefer the transfer of "Will You Love Me Tomorrow" tha appears on the More Dirty Dancing disc over the less dynamic one on the anniversary edition. And the Otis Redding number "These Arms of Mine" is very clearly limited on the anniversary disc, such that the More Dirty Dancing variant is noticeably better. Overall, the "oldies" on More Dirty Dancing sound better than their counterparts on the anniversary disc, but the ones on the original Dirty Dancing soundtrack album sound worse. As far as the '80s material, the original discs are the winners here. The masters used sound great, and they lack the Loudness War volume boost given to their counterparts on the 2007 disc. Obviously, "Gazebo Waltz" is an exception, since it never appeared on either of the original soundtrack albums, but thankfully, it sounds good and is presented at a reasonable volume level. For the '80s material, one would presume the album producers had access to the original master tapes or to high quality copies, and the songs fittingly sound fantastic.
Picking an ultimate winner here is challenging. In the end, it really depends on what you as a listener value more: the older songs versus the newer songs, the presentation, the song sequencing, the overall experience, and which version of "Time of My Life" that you prefer. For overall presentation, the newer disc wins, but I'm not ready to declare its two predecessors as obsolete just yet. For a casual listener, the anniversary disc is probably just fine, especially given that it is still very listenable despite the completely unnecessary volume boost and compression. I'd rather this sonic bastardization not have taken place, but that's just the name of the game these days when it comes to reissue CDs. I created my own version of the anniversary collection by combining the best versions of each song together onto a thumb drive for play while barrelling down the highway on my road trips, and I'm perfectly happy with that.