Matt,
There are so many possible variables .. but let me take a stab at it.
First is helm, your underwater rudder surface and its angle. When going to windward, you want to have a slight weather helm thus requiring you to have the
wheel over to leeward slightly to counteract it. Rudders being symetrical airfoils .. only produce lift efficiently at low angles of attack and start getting very draggy quickly when those angles increase.
Typically, you want your rudder to have an angle between 2-4 deg's.
Anything more and you're overpowered and slowing the boat down.
Anything less and you're not getting the lift from the rudder to windward.
On my boat .. I've actually measured the angular displacement of the rudder (mine is on a skeg) and know the ratio between rudder angle and
wheel angle. Mine is ~9:1. So, I like to sail with my
wheel knot around 30-45 degs to leeward, which equates to about 4-5 degs at the rudder. Anything more and I need to remove main. Anything less .. need to add main.
As you go off the wind and ease the sheets in higher winds .. the weather helm will naturally increase just from the headsail .. forcing you to use more
wheel to leeward and ease the main. If you find that you are luffing your main and speeding up .. you must be slowing your boat down with the rudder.
The solution is to reduce headsail by RF'ing it. This will allow you to re-engage your main without introducing helm that will slow you down. Depending on the cut of your headsail, you need to move your
jib-car forward as you furl it. I've actually marked
furling spots on the foot of my
jib so that I can furl it to the same spots each time and thus know where to put the cars.
Hope that helps.
Angelo