You can't control the weather! The weather during the trip was awful with rain, fog and colder than average temperatures. We knew that the weather was going to be a crapshoot when we booked the cruise so although we were disappointed, it didn't ruin the trip for us. If I was doing it again, I would plan for early- June through mid-September for this itinerary when the weather would be a bit nicer.
With that said, this was our 3rd time on NCL and the first time on the Pearl. The other two trips were on the Epic and we definitely liked the Pearl better. This is not really a ship for children and teens - there are no water slides, splash pads, etc.. If that is what you are looking for, NCL has much better suited ships in their fleet.
There are 2 general population hot tubs and one pool as well as 2 adult only hot tubs and pool. Enforcement of the "adult only" area was a bit lax at times. Because of the weather, the pools and decks were rarely over crowded. The gym was well equipped.
Been here a few times. Unless you are going on an excursion there isn't a lot to do in the town center other than a few nice walks and some touristy shopping
Took the NCL water shuttle (a very nice boat) for the 60 minute ride to St. George when we first arrived. It was on Sunday so all the shops were closed but we had a nice fish sandwhich at Wahoo. 3 hours is more than enough time to see everything within walking distance. Walked around the Dockyard - not much to see and were going to take the water shuttle to Hamilton but it was raining hard so we just stayed on the ship.