Just because Vince was born into a wrestling family doesn't mean he automatically knows more. And longevity doesn't always mean the person knows more.
This would be a valid point you make if it wasn't counter to the point most people use to try and talk up JR's wrestling knowledge. They constantly harp on his 40 years in the biz and his studying the game. Are you trying to say that Vince didn't study the game? He too had to work his way up in the company his father created. HE worked backstage, reffed matches, worked on the ring crew and learned all aspects of the business before getting a chance on air.
He made Shane do the same thing when he expressed an interest in getting into the business. Shane's first appearance was as a ref and occasionally crew backstage during the early days of Raw. And Vince has 20+ more years to study the business from the inside as it were then JR. Sure JR might have been a fan, but he wasn't in the biz or in the know as Vince was.
That's how he knew what to do to get the company away from his father and do the exact opposite of what his father wanted by taking it first national and then global. He ended the territory days his father and his contemporaries had a strangle hold on and turned a small time promotion into the biggest wrestling company in the world. If Vince didn't know what he was doing, he would have folded during the 90's and who knows what wrestling would be like now. But while he made mistakes, and I am in no way denying or defending them, he had a clear vision and focus that allowed him to not only survive those mistakes, but turn them around into back door successes. The XFL failed, but it drew attention back to WWE at a time when ratings where starting to really drop. I actually enjoyed the XFL and felt if they had played up the differences and the entertainment aspect more instead of trying to be completely serious competition for the NFL they could have continued on and been a success. There was some good football played during their one season. Vince might have at times had the wrong people giving him advice but in the end it was his decisions and he took credit and blame for them as needed. But lord help you if he trusts you with a task and you fail, because then you're on his bad side and that doesn't work out for you.
You want to use your baseball playing as an example then I'll use my football playing as an example. A close friend of mine and I both played football. I played one year of JFL and one year of high school. He started playing JFL as soon as he could and played all four years of high school. However he never took the time to study the game. When he watches games on tv he doesn't pay attention when they explain why players do what they do. It was very evident when we coached JFL together that he really didn't understand the game at all despite playing several years. I had to share my knowledge with him to help him be a successful coach. If you want a wrestling example watch CM Punk's dvd where they talk about how much time he spent learning everything he could about all aspects of the business while the other guys came in, trained and went home. By all accounts Jim Ross is a student of the game.
As far as him not wanting to go into wrestling that may or may not be true but that doesn't mean he wasn't a wrestling fan growing up. That doesn't mean he had zero interest in wrestling. Do you know his background?
He worked one night as a wrestling announcer and then worked three years as a referee before taking time off and coming back as an announcer so I don't really know where you got your "his friend got him a job as an announcer" story from but it's inaccurate.
Guys like Jesse Ventura and Bobby Heenan were color commentators. That's completely different than being a play by play guy like Ross was. He's there to call the moves. They're there to tell the stories, entertain and/or explain things from a wrestler's point of view. The two are meant to compliment each other. He wasn't meant to be able to explain things from a wrestler's point of view.
As for where i heard about this, there was a series of interviews a few years back, not sure if they are on youtube, but they were aired as vignettes on raw and smackdown and they talked about JR's early years and how he got into the business. It think it was around the time he 'stepped' down as head of talent, when he 'retired' for the first time in the early 2000's before they brought him back. he's also been known to say in many interviews that if there was any job other then wrestling he had always wanted to work as an announcer/play-by-play for football. Usually mentioning doing so for his college/university team. Oklahoma Sooners, I believe. I think it was brought up when he did an episode of Off the Record with Michael Landsberg during a Canadian tour a few years ago.
JR's general match calling ability is what I am questioning. As I said in several posts, he's at his best in spot moments as he can rev a crowd during those 'omg' or 'wtf' momentary bumps in the match. But he has a bland voice when it came to describing the wear down and actual wrestling moments. He couldn't draw focus or crowd reactions to say, a headlock, or chops in the corner. As good as some of his sound bytes were, he failed at making the rest of the moves sound interesting. For every one of his 'Oh my god, they broke him in half!!' there was a half hour of 'oh, a series of chops, a headlock, that looks bad for him' that was delivered in a almost bored tone. He was good at those big moments, and the interplay between him and who ever was paired with him was sometimes very brilliant, but as a play by play announcer who's job is to make us excited by even a quiet moment in the match, he failed. He was more of a color guy himself then a play by play, so it was like they had 2 color guys instead of 1 of each, and this is why they often brought in a 3rd commentator who was mainly focused on calling the match while JR and Heyman/Lawler/Cole sniped at each other.
As for you and your friends experience, this is an example of what I'm mentioning. Your friend played a lot longer then you, but didn't understand what was going on around him, even though he was around the inside a lot more then you. Why do you think JR being around for his time means he learned and studied more then Vince? You think Vince doesn't understand very aspect and point of the business? Where did you hear that JR made this immense and intense study of the business? As every one has said in every shoot promo its brought up, Vince eats sleeps and breaths wrestling. He has seen it all and done it all in the business and his mind is constantly working on finding ways to improve the product and expand into other avenues. From what I recall from interviews, JR watched wrestling as a kid, but it wasn't his major focus. He was focused on football and wanted to work in that field. He stumbled into wrestling and decided to stay but if at anytime during his life a job had been offered to him as a football announcer, he would gladly have left wrestling behind.
His one night worked as a announcer, how do you think he got that job? You don't just come out of nowhere and walk into an arena and say, i'll be the announcer tonight. Some one helped him get that job. Then he was a ref for a few years, and learning the business on the go before leaving and then coming back.
Now, I'm in no way saying he doesn't know the business very well, I am just saying I am tired by people assuming he automatically knows more then Vince, and most of those who argue the point at some time bring up his 40 years in the business, leaving out Vince's own tenure in the wrestling world. Vince has made some major f)))ups at times and there is no denying that. Would he have been better server listening to JR then some of the people he did? More then likely. But don't dismiss Vince's knowledge out of hand because he let his ego cave into to ass-kissers who led him to make mistakes. Vince knows wrestling. He just doesn't know modern culture and how to make the two connect.