I think ours is about as large as I would want to go as far as rigging it and I think it is designed for boats quite a bit larger than ours, but I think our lighter boats probably sail on anchor more. At least that is the case between our two boats. From the one trip we did take with the Endeavour I don't think we will need an anchor sail for her.
The sail is a sail and the way it seems to work is that it sails the boat off in one direction and then keeps it pretty much there. Of course the wind isn't steady even though it seems to be and you still move some. Since is a sail if I think the winds are going over 25 I'll take it down.
I can rig it in just a minute as I added another uphaul line and block just for it and the bottom lines are fixed once you set them up once and snap on with carabiners. I found that by raising it some above the solar panels higher on the backstay that it was more effective.
As far as an anchor our 22 lb. claw worked very well in Canada and Idaho and I'd think you might be in similar conditions. We never drug anchor there. We now also have a 25 lb. Manson that I think is a better anchor, but if you didn't want to spend that much the 22 lb claw is great.
Two anchors off the bow would help in either a Bahamian style moor or in a "V", but I'd never put out a stern anchor in those conditions unless you were 100% sure the wind was going to be in the same direction all night.
You know we finally got so use to swinging on anchor that we don't even notice it. I think I use the sail more as something else to do to keep me busy

. We use the anchor alarm on the Garmin 76 and it is amazing when you look at the distance you have traveled on anchor in 2-3 days. Set the alarm right where you drop the anchor and before you back down and the alarm can be set for a smaller radius,
Sum
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