I wonder what the percentage of the sox-game viewing audience "We" are? Do you really thing that an intelligent approach would be speaking over the heads of 95% of the viewing audience?
I think that we're a very, very small percentage of baseball fans. Have you ever heard sports radio callers, spoken to people in the office about last night's game, listened to people blather on in a bar? And I'm not trying to be exclusionary, because I love television and comedy, but if I was in Los Angeles and was talking about my theories on TV and comedy, I'm sure some guy more plugged in than me would be making that wanky-wanky motion with his hand behind my back.
You have to remember that it's a broadcast, not a narrowcast, so NESN (or ESPN or FOX or MLB Network) can't cater to you or us specifically. They have to remember that there are 8-year-old boys, 78-year-old men, 21-year-old women, whomever are all watching the game and may want to listen to a "personality" like Kay or Hawk or Remy do their shuffle rather than explain why a bunt is stupid in just about any instance.
What if NESN, once a month, ran an alternate telecast on NESN Plus that catered to "Us." They could use the same camera feed, except when it goes to Don/Jerry, and "Our" announcers wouldn't even have to be in the booth, but could broadcast from NESN studios.
So hire two more announcers, open up NESN+ and broadcast it for the less than 5%? I may be wrong, but that's way too expensive for a good ROI for NESN. NESN knows that we love the Red Sox and we're going to watch whether they have Rob Neyer and Keith Law (or whoever) or Don and Psycho or two trained chimps hurling feces at each other. They aren't going to spend anything to bring us in, because we're already in.
To answer your question, I think that Darling is pretty good. I thought that Tito was very good. Leiter is above average. Eck is very good. They're all better than Lyons, but Lyons is better than a bunch of others. In general I think we've all come to accept mediocrity for these positions even though they'd seem to be jobs that would attract top talent.
I think that this is the point. Lyons was perfectly average last night, he didn't do anything too stupid, his voice sounded pretty good, he (for the most part) did his homework. He didn't get in the way of my enjoyment of the game (unlike Nick Cafardo or Frank Viola -- who seemed nice and interesting enough, but his voice sounds terrible). And Darling, Tito and Eck are all very good, I agree but after awhile you'd get sick of the stuff that's coming from their mouths too. Fifteen years ago, Remy could do no wrong, now people want him out (before his son's prison sentence). Same thing with Tim McCarver. There aren't a lot of good color guys because it's a hard thing to do well and there's a certain shelf life. Because of that, I don't think that this job would attract the top talent that you think.
For one thing it's hard to talk about something every single day for three hours and be interesting and engaged and have something relevant to say. Plus, there's a lot of work that needs to be done prior to game time. Third, you have to have a talent for it (voice, poise, knowing when to talk and when to STFU), this isn't an easy thing to say. And most ballplayers when they're done have enough money to do nothing for the rest of their lives, why would they want to work hard at a gig that has a ton failures? You really have to think that you're something special to get in front of the camera day after day after day.