I had a 2002 account that I lurked with but either got banned or forgot the password (can't remember) and then didn't create another one until 2007. But yeah living in SoCal in the 90's, there were a lot of guys plugged into the MMA scene and a fair amount of wrestlers and BJJ guys cross-trained or at least were aware of each others' games. Rickson and Rigan had gyms in Torrance and I trained at Rigan's a few times and rolled with a guy who had just left Vitor Belfort's new gym after his UFC debut. Also got my ass kicked many times at open mats by Francisco Bueno's coach, who was a HW college wrestling All American. Apparently Bueno was a good fighter but is most famous for getting KTFO by Vovchanchyn.
Those early years were something that can never be repeated, not really "the glory days" of MMA in terms of performances in the ring or cage, but simply the glory of mystique of style vs style as people had dreamed of for decades watching martial arts movies, and the excitement of finding out what works in real time, and adding another layer of the puzzle to get to where we are now. Its this adventure of discovery that is largely completed now in terms of MMA that people who only got in post 2010 had missed, as I would say by then people mostly knew what worked in the cage after Machida put Karate at the UFC gold and shut up the TMA haters.
Its a bit strange though you say you trained with some of Rigans guys in the early 90's but its only by 2004 you realised it wasnt " Just Judo" they were doing. I mean surely when they were rolling around in guard which isnt generally worked in Judo that let you know something was up.
Most Judo schools have limited newaza although there is also the suggestion made on this thread that Judoka would have done way better against the football player, not simply in securing the throw or takedown but in the explosiveness on the ground even that characterises the rapid Judo ground game.
I know you've posted about Wing Chun over the years and I think that's cool. I trained it for about 6 months (along with escrima) under a Filipino guy I was stationed in the middle east with in 2000. I think the fundamentals are sound and it can be effective for self defense. But I'm always wary of style vs. style debates because I've trained long enough in enough styles to know that any style can be effective in the hands of the right practitioner. The LAPD instructor guy who introduced me to BJJ in 1991 was a high level Aikido guy who preached the importance of strength training and being well rounded. He had trained with Rickson and Helio and had brought in Rickson a bunch of times to train with the local college wrestling team and their coach. The HW wrestler I mentioned above was one of his students (worked as a LEO) and he could wrist lock the shit out of you if you tried to tie up with him. But guys get into trouble when they think their shit doesn't stink and their one style is the right tool for every situation.
Opinions on here of 'what definitely works and doesnt work' have been proven time and again to not mean shit and keep evolving.
I have been here long enough to not be triggered by the criticism. Sure, Wing Chun has received criticism because the few one dimensional guys who entered were taken down and beaten as expected and because since Bruce Lees time it was widely considered to be "The Ultimate combat system" but opinion has gone the opposite way now. You could say MMA training has replaced that mantle to an extent but in a free fight a top level WC guy is formiddable at close range and if you train grappling as well to cover that weakness I dont see how its not a complete combat system. I am very glad I chose that style all those years ago and it integrates very well with Judo, handfighting and control and knife work with escrima as you mentioned.
Dude I would highly encourage you to stop making excuses and find a Judo dojo. Judo is forgiving with older guys. If you're 40+ with old injuries or whatever, you can just drill the moves and skip randori if you want to, and no one gives a shit - there will be other old guys in the room doing the same. But I can tell you that proper ukemi taught by a proper Judo instructor will save your ass in daily life. Also Judo grip fighting sequences and set ups taught by a proper Judo guy would chain very well with your wing chun.
What deters getting back to Judo and finally working to get that coveted blackbelt which I could do probably in 18 months - 2 years from where I am, is that being thrown and getting up repeatedly doesn't seem as appealing as when I was younger. Randori is part of the style like Chi Sau in Wing Chun so you cant just bypass it.
Then there's the fact that given the evolution of grappling, a Judo blackbelt doesn't mean what it was in the past as you still have difficiency in leg lock knowledge and other areas on the ground. So nogi would probably be the more interesting one to get into but again, my concerns are getting knees regularly twisted the wrong way isn't healthy at all and I think a lot of guys overlook old age and mobility concerns which will be in their reality sooner than they think.
I think the most I would do is an occasional open mat as it would be fun to toss some BJJ guys around and to work on a purely defensive game shutting down submission attempts and returning to the feet from the ground and generally imposing my game on them and reminding them that Judo is the father of BJJ.