I can remember watching an interview with Sullivan where he admitted putting Konnan in the DoD was a mistake and he wasn't right for the group. Goes without saying he was a much better fit in the nWo, Wolfpac and Filthy Animals. I didn't realise until reading the Observer rewinds on SC how big of a deal Konnan was in Mexico. Almost Hogan levels of popularity. Yet WWE gave him the stupid Max Moon gimmick, and WCW shoved him in the Dungeon. He got over to a degree as part of the nWo and was very much over in the Wolfpac, but was never more than a midcarder at any point. I guess his size worked against him in the US to some extent.
When I watched the Sting/Regal feud I was a bit baffled by the homophobic stuff. It's not like Regal was Adrian Adonis or Goldust. I assume it was just posh = gay or British = gay? I don't know, but it was certainly unnecessary.
I didn't have an N64 as a kid, just a PlayStation (and Genesis), so I never played the classic N64 wrestling games. I had WCW Vs the World which was... okay, but slow. It was basically a reskinned Virtual Pro Wrestling, which was a Japanese game originally. At the time I had zero idea who all the foreign wrestlers were, but I would have appreciated that more as an adult. Although renamed, the game included Jushin Liger, Akira Maeda, Muta, Hayabusa, Taka Michinoku, The Great Sasuke, Stan Hansen, Hiroshi Hase, Sabu, Shinya Hashimoto, Bruiser Brody, Kawada, Mil Mascaras, Terry Funk, Ken Shamrock, Keiji Muto, Jumbo Tsuruta, Road Warrior Hawk, Onita, Tenryu, Kobashi, Giant Baba, Karl Gotch, Dr Death, Inoki, Bas Rutten, Dynamite Kid, Super Delfin, Misawa and a few others. Basically a dream roster if you were into Japanese wrestling at the time.
I spent a lot of time playing WCW Nitro and later Thunder, which is unfortunate as both games suck. I also played a ton of WWF Attitude which was, again, okay without being great. As I hadn't played the N64 games I guess it was a case of ignorance is bliss. I didn't realise what I'd missed out on until many years later. I got WCW Mayhem and thought it was shit. Barely played that one. I never got Backstage Assault, and thank goodness for that, as by all accounts it is awful. I think I may have picked it up from a second hand shop some years ago for £1 or maybe even less, just to say I had it.
Things did pick up hugely when the PS1 got the Smackdown games, which were genuinely great and I played them a lot. The PS2 Smackdown games were also excellent, so it worked out in the end I guess.
The last WWE games I picked up were 13 and 15. I actually quite liked 13, especially the ability to have your own music and titantrons on the 360. That was very cool. Didn't play much of 15 though. Fight Forever I'll probably only play a little bit of, but as you say, for £8 it's a steal and I'm not sure it'll be much cheaper than that for some time.
As for Undertaker and Trump, yeah, can't say it surprises me. When watching classic stuff I can separate the character and the man, but it's certainly disappointing that IRL he's such a dick. Not really a surprise though when you think about childish stuff like "BSK" and wrestler's court, as well as being Vince's right hand man for decades. The signs were all there that outside of the character he was a questionable person. Kane is arguably even worse, as he actually had a reputation as one of the smarter wrestlers and a good guy... but as it turns out, no, not really.