Every plebe event is different for every family
My guess was the %/# of plebes who had a family member with them at R day was high, my guess 75%. Many came with large families a day or two early to see WP or NYC; a "last family vacation" sort of thing. Our son wanted none of that. He wanted time at home and we drove up early on R day without mom or siblings. Stood in line for 30 minutes, chit chat with families in front of and behind us. NONE of the new cadets were interested in engaging in conversation. I did chit chat with my son; even he didn't want that. Finally asked him the big question (are you ready, nervous, excited, etc) and he replied matter of fact "he wanted it over" and wanted on that bus to end the 30 minutes of waiting, 30 days of waiting, months of waiting. I left R day early before the oath, I just wanted to get home and knew he wouldn't know if I was there or not.
Folks have said here A day had no real events for families, which was true. However, your child will not mind being with family and relatives and you will not mind just watching TV in a hotel room with your child either. The lunch on Sat away from West Point is huge for them. However, be prepared that your cadet may sleep in your hotel room as you go out for meals Sat night and Sunday.
I was surprised posters mentioned PPW was a disappointment since plebes are just counting the hours until they leave for spring break. That is entirely true but the chance to meet your plebe's friends and their families is worthwhile; not to mention their professors, the banquet, uniform factory, etc.
Would clearly rank A Day first, then PPW (you have time to decide since this is Feb), R Day, and tossing in a football weekend if you can, perhaps ahead of R Day even. Your mileage will vary, however!!!