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Gonna ramble a lot here.....but I think one stumbling blocks of wrestling winning over new fans is because of the misconception that people watch wrestling because they believe it's real, and people are far more likely to embrace it the moment they get over that hurdle.
I think a TV show like GLOW will win over far more fans to wrestling who never would have considered it before than any number of neckbeards with a pre-planned "BUT THE HAZARDS ARE REAL" diatribe to unleash any time someone tells them it's fake. Because wrestling fans shouldn't be defensive of wrestling's "reality, we should embrace everything that makes it silly and ridiculous, and celebrate that.
Again, it's about creating an emotional investment - even if that initial emotion is nothing more than curiosity, that's a foot in the door that you're far less likely to get if you cling to the notion of wrestling as a legitimate sport.
I think it's great early on to let new fans know what your company is about. A casual audience are going to come in with some variation of the "it's fake and gay" preconception, so you have to hook them right off the bat. A comedy match is great for this. Not full-blown shenanigans, but something that's got a decent amount of "real" wrestling in there so people know that you're capable, but enough comedy that people in the crowd realise that the company is in on the joke.
Then they're not snickering behind their hands at the inherent silliness of wrestling, they're invited to join in, and the performers are telling them, "it's okay to laugh at this bit". Then they open up, they'll laugh out loud, and then they're invested, and suddenly they're part of the show. Once you've broken that barrier, and got them laughing, they're ten times more likely to start cheering, booing, chanting, and participating.
The other way to try and dispel that "it's fake and gay" criticism is to go the entire opposite direction - give the crowd an "Oh shit!" moment right off the bat. Throw out something that impresses even the most jaded person in the audience enough that it'll break through that barrier and just get to an instinctive reaction.
Depending on your company - this can be where you throw in some "spot monkeys" and flip-de-doos that nobody in the crowd can do. Or if you're a more hardcore-focused promotion, maybe you start off with a clusterfuck brawl that spills to the outside and you let the fans really hear the chops and forearms right in front of them. So even the jaded fans think "well, that had to hurt".
Basically I think you win over fans by giving them an "in" to your world, to effectively say, "it isn't a real sport but, look, that doesn't really matter".
That can be comedy - and I do think that's the best way - it can be a big move, it can be a compelling personality or story. But what I don't think can ever manage to win over a new fan, certainly not an adult fan, in this day and age is sticking stubbornly to an insistence that pro-wrestling should be treated as a legitimate sport.
If somebody isn't already a fan, they're already going to have a world of preconceptions as to how wrestling absolutely isn't that, and a reasoned argument with the best of intentions will never be enough to change their mind.
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