Well, figured I'd post a follow-up. Our guide was very nice and accommodating as we were up front with the fact this trip was our first in a while but also a test run to find out if evening coming on a regular basis would be something in our future. I decided to go into it not to press anything and to see if her comments squared with what I knew from my research here. It was also clear to her from my responses that I had done my research.
Overall she said nothing surprising and did a good job of making my skeptical wife lean forward a bit. She did not mention anything about Riviera restrictions and I didn't press. One thing that did surprise me was they are offering 2019 points if you buy a December use year and you would only have to pay 2 weeks worth of fees.
When I follow up with her over email I'll bring up the restrictions and see where that goes. The annoying thing is I really think Riviera would be a perfect resort for our family, but I am nervous about how the restrictions will effect everything.