I was hesitant about jumping on the Waves Wagon because of their WUP, but all of the plugs I've purchased recently are version 9 and fully compatible with Windows 10, so I think they're future proof for a while yet.
I agree that Cakewalk's CA-2A is top notch, I really don't use the CLA-2A at all because of that fact. However, not being a huge fan of the ProChannel, I do prefer the CLA-76 over Cakewalk's emulation. Even if I was a ProChannel guy, I still prefer the CLA-76 over Cakewalk's. I won't go as far as to say it's better, I just prefer it. Same with Waves SLL Bus Compressor, although Cakewalk's is pretty good.
Regarding stacking, yeah, that seems to be a pretty common practice. Grab the peaks with one compressor, smooth things out with another. Sometimes the 1176 will get hit first then the 2A, sometimes the opposite. I'm also a fan of FabFilter plugins so I'll often use the Pro-C 2.
One thing I've found, especially with the modeled compressors, is that it's really easy to overdo it. I absolutely love the character of the 1176, especially on vocals, but my voice in particular gets pretty harsh and honky if I'm not careful. Plus there's always the issue of sibilance whenever you're doing a lot of compression. That's probably my least favorite part about mixing vocals. These days, it's pretty much standard for a lead vocal track to go through a lot of compression to keep everything audible and on top, but having to fight that with a De-Esser or clip gain automation is a pain. (And I do a lot of vocal stacks, so the issue is amplified in my case.)