I usually take 7-8 college kids in June out on the boat...some thoughts IMHO

1) You could stay at one place for the whole time and they would have a blast...i always have to slow it down per their request and save some for later
2) I always ask them what they would do differently and they always say they wish they had more time
3) Last trip of 14 days-I asked If you had one more day where would you go back to (A Cane Garden Bay). One less day cut what (A Cooper Island)
4) Get noodles for snorkeling for floatation and visibility especially out on Anegada reef with Sherwin or Kelly
5) I like your idea of starting and ending at Norman for a quicker sail back...or 2 days in Anegada which you keep hearing lol
6) My son is a marine scientist and his favorite part is the day trip to Anegada reef (we use Kelly but either is fine)
7) Besides weather check your north swell if at certain spots (Guana, CGB) https://marine.weather.gov/MapClick.php?zoneid=amz715#.YpITtijMJ3j
8) At Monkey Point Guana have 1 person go in person to the dinghy line and check snorkeling conditions before everyone gets in, It can be hit or miss
9) After Wonky Dog head over to Potters for night life
10) Diamond Cay is great call...
11) Bring some pennants the kids can sign and post. We still have college flags at Cow Wreck from one of our kids trips

Hope you make it to Anegada...our first time I navigated up using Walkers chart and was very stressed because I knew we couldn't see it and didn't want to miss it...about 1/2 way up we looked back and realized we could see Gorda peak the whole way up...duh

Do you have Scotts Guide to cruising the BVI? I give that to the kids in advance with the itinerary so they can read about what you are going to do. I can also send you my expanded trip plan and essential items to bring for past years if you want

Have a great time