Hello ArgleBargle (coming to you from the cafe at the Virgin Gorda marina)
1. Mooring balls are a bit like parking spaces the mall. Sometimes, even when the mall is full, you can find a good spot quickly; other times you seem tonot be able to find one at all, even when you feel you should be able to.
The popular anchorages can fill up starting at about 4-5pm. The Bight is often quite busy, but rarely 100% full, and you have a couple of options just outside the Bight as well. I've never seen the North Sound full, but there too you can anchor off Prickly Pear or motor/sail to Leverick Bay for more mooring balls. Anegada doesn't have many mooring balls, but lots of room to anchor. Great Harbour on Jost Van Dyke has no mooring balls and I would recommend getting there early in the day (but not before 10-11am) and to set your anchor in peace and quiet and then dinghy or walk over to the Soggy Dollar
2. Wind and waves are typically similar most of the season. 12-20 knots and not a great amount of waves unless you head out to Anegada, in which case you might get a atlantic swell but chances are it will be hardly noticeable to someone from rougher waters.
3. I've head charter guests call back to base on VHF to demand immediate repair and monetary recompense because 1 of their 5 showers isn't working. With that mindset any charter company will be unlikely to make the customers happy. Stuff will go wrong. So far my only negative with Footloose was assisting some people whose transmission failed on their 52'. This happened in the late afternoon off JVD and Footloose didn't have a spare boat so the next morning they proceeded to replace the transmission while the boat was anchored in Great Harbour. I think small stuff always goes wrong and much more of that will break on an older charter than on a newer one. That is part of the price difference between the two type of boats.