I would definitely agree with the other posters that OO BIP is a great alternative to VR28 Black Iridium. I'd also recommend Daily Prizm as a solid alternative for that similar rosy tint.
If you're deciding between the Tincan and the Tincan Carbon, I would definitely suggest going for the carbon version. I mean aesthetically they both look fine but the Carbon version is so much more comfortable around the temples.
From what you named, as other people have said, I would definitely check out the Badman. I would also potentially look at Offshoots and Big Tacos for O Matter and Plaintiff Squareds for wires.
I would go with Prizm Road if I had to pick one. While Prizm Trail is awesome when you're going in and out of shade since it provides a lot of sharp, bright contrast, Prizm Road will hold up better on your basic sunny day and has enough versatility I think to handle medium light as well.
Haha I do agree that there is a lot to like about the Jawbreaker but I wouldn't say it's the consummate pair as there are one or two things I'd tweak but for cycling I can definitely see some legitimate improvements over the radarlock. In terms of every day use, YMMV.