I am finding Simon Gerrans's commentary very interesting.
Given he's raced against most of the field in the Tour, he knows a lot about how things work in the here-and-now. Having a recent UCI Pro Tour veteran is gold for getting the best intel. His profile pieces on things like Caleb Ewan's bike are simply awesome: informative and candid, very clear.
I'll admit that Adam Blythe has been a great asset for the NBCSN crew. While I really like Steve Porino, he's a skier first and didn't grow up inside the pro cycling circuit. Blythe did, retiring in 2019 so he's a familiar face to the teams and the ASO media folk. When I choose to watch NBCSN, I enjoy Blythe's insights when they check in with him.
I'm also enjoying Chris Horner's YouTube
post mortem commentary about things like finishing sprints, pacelines, climbing tactics, and the like. He's smart, and I can see why he's made some good money with race coaching over the past few years.
Is anybody here watching GCN's Race Pass coverage (in partnership with EuroSport)? I've seen some of Bradley Wiggins' bits and they're insightful - he knows what's going on and is more than happy to share his opinion.