A recent thread that I've been participating in, On Skilled Play, had me thinking about this thread again, and my own experiences with the OSR.
My initial impressions of persons who consider themselves OSR was frequently one of arrogance and derision towards other playstyles. Please don't take that as anything other than a personal opinion intended as the basis for constructive criticism. I've met quite a number of OSR players who are anything but arrogant or derisive. I'm just speaking in general terms of my own initial impressions based upon interactions with some who espoused this style.
Admittedly, I reacted emotionally, causing me to reject the OSR play style out of hand. It wasn't until some more even tempered OSR folks explained things in a way that wasn't condescending that I realized that this play style actually had a lot going for it.
Some of this has to do with terminology. There are quite a number of terms floating around in OSR-related theory that can come across as more than a little pretentious. Such as "skilled play". Now, there is NOTHING wrong with the concept itself. It's a fun way to play for many people. The name seems a bit loaded though, right? By calling it "skilled play", there is an implication that other ways of playing aren't skilled. That's obviously false, as there are plenty of other ways of playing that utilize different skills.
Another one is Combat as Sport vs Combat as War. I've often seen a strong implication from some CaW advocates that CaW is for "real men", and that CaS is for babies. Which is patently absurd! Everyone know that TTRPGs are for babies; "real men" LARP!
The point of this, again, is not to attack the OSR or the people who consider themselves a part of the OSR. I've conversed with plenty of nice OSR players who didn't come across that way the least bit. This is not meant as a blanket statement of how the OSR IS, but rather how I initially perceived it. (I doubt I was the only one.)
Oftentimes what I saw, when the OSR was criticized along these lines, were responses that were something like, "Too bad your feelings got hurt. Sux to be you". This too left a bad impression on me.
What I'm trying to say is that I think that this kind of behavior is not good for the OSR, and it won't really help to attract new blood. Certainly not a everyone in the OSR behaves this way. It may very well just be a loud handful of people. However, I initially rejected the OSR out of hand because of it, and I wouldn't be surprised if others have as well.