I am getting the Stainless Steel case, 38 MM, with black classic buckle. In the article below, CE Pro talks about Lutron Caseta's support of the watch with new watch apps. I think the issue here will be that Caseta is a cloud based architecture (easier to update) whereas RR2 has its protocol on the home LAN. I hope Lutron will support both Homeworks and RR2. That customer will be more inclined to buy the watch and they will expect it to work since they shelled out quite a bit more for a higher end solution.
Lutron is Watch-enabling its Caseta wireless lighting control and Serena motorized shades, which connect to the cloud (and ultimately the Watch and other smart devices) via the company’s Smart Bridge and Smart Bridge Pro gateways.