I think Rory is the real deal, but I agree with you that training is always better than not training
True about both.
You have to be around Rory a while to get to know "the real Rory." Often he shows you only a small part of the real man. But underneath it all, he is indeed the real deal.
As for training... I think Rory himself agrees with this. Rory trains TMA himself. And (surprise) he recommends a lot of tactics and approaches to real-world violence that are similar to his core style (sosuishitsu ryu). No surprise there...
Which comes first, the chicken or the egg? Did Rory get lucky and start with a style that fits real-world combat well? If you study your history, you'll see how this could be so. And interestingly enough, many aspects of Uechi Ryu (e.g. close-in fighting and a principles-based approach) fit in with what he likes in a martial art.
Also... The thing I *like* about Rory is that he helps explain and validate what I have found to "work" in self-defense. Before I knew contemporary thinking, I called what happened as "my body acting without my permission" (presumably from years of training). Now I know that I short-circuit the OODA loop. Whatever... it works for me!
Also... It's been difficult for me to communicate how things that most people would consider "non-martial" have been my best assets in self-defense situations. Rory basically comes to the same conclusion. How does all that happen? All I know is that it can. Perhaps my techniques and information evolved to knowledge and wisdom over time.
The fact is that 99.999% of people just don't ever get into those situations to get the "real world" experience and it isn't feasible to ask them to! I've said that plenty of times. The first time you get into a "real world" situation where you need the knowledge, you don't have experience on your side... just training. This is true for subsequent "real world" situations as well. I'm not sure exactly "when" experience becomes "enough" or the over-riding factor, but IMNSHO, it isn't really early on. Personally (as you and Van-Sensei know) I had a number of "real world" successes before I had a very "real world" failure. I don't wish failure on the street on anyone, but I learned more from failure than from success. It took a lot longer to learn, but it has helped me... and it has helped me to be successful more and better since. I also not just believe, but know that earlier successes set me up for failure (for various reasons too numerous to discuss).
All this makes me think about my line of work where we try to judge MDs by their bad outcomes. It turns out that these events are so rare that you really can't judge most MDs by the few experiences they have. "Stuff" happens, and it takes many, many man-hours of experience before conclusions can be drawn.
Another thought... I have to wonder about how much of being an "experienced" self-defense expert is by nature, and now much is by nurture. Would Rory have been good even without some really good training? Probably. But he's better with "the right stuff." Meanwhile, a lot of people can learn all the right stuff, and never repeat the successes that Rory is fortunate enough to have experienced.