Have you considered backing in
It makes it a much easier escape if things go wrong. And the propwalk is mostly in your favor. Be carfull the propwalk and the bow windage does not push the stern too far too port, but if you judge it right it will help turn you into your berth.
Good suggestion. Backing in is an option, but we prefer to be bow in. That gives us a nice view of Mt. Rainier thought the harbor entrance and gives us a bit more privacy. Even backing in though with the wind from the North the bow tends to fall to leeward.
1.You need a bannister line. It makes it easier to leave your slip.
2. To return to your slip, come at it from downwind, rather than trying to enter the slip with the wind. In other words, pass your slip, turn around, and nose in with the nose into the wind. Use a boathook to loop a knotted springline loop over a cleat on the upwind finger, and power into your slip pivoting off the springline, then tiem off the aft dockline first.
I don't know what a bannister line is?
Not sure how to approach the slip from downwind unless I was to back down into the fairway past my slip with my bow into the wind, then stop and go forward turning to port into the slip. Is that what you had in mind? That would work, but the fairway is pretty darn narrow to make a 135 degree turn to port.
Since you have a float on either side, I'd just put out fenders (or fender the float if that's permitted) so that you land on whichever one is easiest. It's a simple matter to tie the boat from the other side once you're stopped...
And.. have you considered tying the boat from both sides and keeping her 'suspended' between fingers to utterly eliminate fender rub?
I think that is what I'm thinking will work the best. If the wind is from the North, then land on the Port side and retie the boat after wards. I use a Port side bow breast line now that keeps the boat off the fenders on the Starboard side for the most part unless their is a strong South wind. We have a hill and condo to the South that gives good wind protection from that direction for the most part.