Hello & welcome!

The likelihood of an early start is slim to none on your first day unless things have changed since our last charter. It would require you to be able to do all of your checkouts the day you arrive & in our experience that's rarely possible, especially as a first-timer. I'd plan on Norman, Cooper, or Peter for your first night.

Sailing up the north side of Tortola to North Sound can be rough depending on conditions. If the weather is perfect it can be a decent but very, very long uphill climb, but if the weather isn't perfect it can be a real bear. Down from Jost & then up the channel is a VERY long upwind slog, especially if you're not on a very big boat. I wouldn't try it... On our trip a couple weeks ago we went from Soper's to Scrub on our first day & it took almost 6 hours in well over 20kts of wind. Just depends on wind, waves, vessel, and sailing ability... But it's a long way.

Unlike every normal, reasonable person here, I almost always have a set itinerary & we've only had to abandon it once or twice over the years due to impossible conditions. But I think you're trying to bite off too much with doing things in this order.