....
I was thinking of using a drogue from the bow of the boat to keep it
pointed into the wind for raising/lowering sails. Is this practical?

No it isn't. I find that when I want to get underway offshore without
using the engine that raising or unfurling the jib and then putting the
boat as hard on the wind as she'll go and then raising the main works
well. I only drop the main either in a big squall or in a calm while
at sea, in either case I find I can get the main down on any point of
sail. However, if you have trouble you can reverse the hoisting
procedure. In any case, drogues are a pain and sea anchors are a major
pain.

-- Tom.