We have to back our 32' (39' LOA) schooner into our slip because we have a very short figure pier and can only get to it from aft (the
bowsprit is too long to let us get close enough if we go bow in). Like you we have a good amount of windage.
As suggested above you may want to take your boat out on a calm day, away from anything to hit, and practice backing to see what your boat does. It's probably going to want to pivot around the fin
keel. Which way does your prop "walk" the stern, when you are in reverse? You'll want to take all of these things along with windage into account in figuring out your strategy for backing down into the slip, and come up with a strategy that uses your prop walk and windage to advantage, rather than fighting it.
Here's how we do it: the prevailing
wind is a crosswind from port to starboard when backing down into the slip. Our prop walks pretty significantly to starboard. So, when we come into the harbor I get lined up perpendicular to the slips, with the slips off my starboard side, and rather close to the
outboard pilings (this puts the
wind more or less on my stern). At this point I'm usually coasting in neutral, giving bursts of forward
gear as need to keep steerageway. About one slip away, I execute a turn to port. I can sharpen this turn as needed by (a) more bursts of power in forward, and (b) bursts of power in reverse (which pulls my stern to starboard). The objective is to get lined up with the slip and not too far out, so when lined up I can give her a burst of reverse to get steerage, then go back to neutral to cancel out the prop walk and drift back into the slip.
As suggested above, I have lines running from each
outboard piling, back to the seawall, so I can reach out and grab a line to pull the boat back into the slip (my boat displaces almost 13,000 pounds and I have no trouble pulling her back by myself, and I'm no body builder).
Lately, what I've done is get the boat about midway back into the slip and then cleat down both bow lines. I have them measured out so that at full extension they still hold me off the seawall. I then put the boat in low reverse; it backs down until the bow lines are taut and then just sits there while I get the stern lines and springs on.
It took awhile to get this routine down and for awhile I put on quite a show for the restaurant at the marina every time we docked. Now we have it down pretty consistently.
The trick is getting your prop walk to work for you. Given the set-up you describe, if your prop walks your stern to port, you may want to try a similar techique: come in perpendicular to the slips, execute a sharp starboard turn using forward/reverse bursts to pivot your boat around to line up, then give it a burst in reverse to give moving and then coast far enough back into the slip to get on a piling or line to "warp" (i.e., manhandle) yourself in.
If your prop walks to starboard, then you may want to come in on the far side of the fairway and go past your slip, execute a sharp turn to port, use the forward/reverse routine to pivot the boat around to line up, and then back down into the slip. With some practice, once you know which way your prop walks the stern, you'll be able to spin the boat around more or less in it's own length.
I don't use a lot of
rudder movement in the foward/reverse pivot move. I have the
rudder set to the way I want the bow to turn when I'm in forward
gear. I don't move the rudder when going into power reverse - my prop walk is sufficient to overcome it. One moving in reverse with
transmission in neutral, I can use the rudder for directional control. I find it helpful to be in front of the
wheel facing backwards, so the
wheel movements are just like I want the stern to move - turn the wheel left (actually to starboard) and the stern will move to the left (actually, starboard, but backwards).
As to windage, if generally the wind is blowing parallel to your slip and from the shore, you can use that to help in whichever way you pivot - my experience is that the wind tends to catch the bow and push the bow off to leeward. I have to compensate for that with my technique by pointing slightly upwind when I come thru my turn so that I'm not exactly lined up with the slip but actually pointing a bit to windward of it. My prop walk to starboard helps to offset the wind pushing the bow off to starboard.