Psneeld wrote, "[D]on't commit to a side just because you rigged based on a dockmaster assignment and suggestion."
Amen and amen. Learned that one the hard way one day when I entered a yacht club via its narrow approach channel, bound for a dockmaster-assigned starboard-side tie to a face dock. (Those who have visited the Field Club in Sarasota will appreciate the situation). My vessel at the time was a 46' Morgan ketch. The wind from an approaching cold front was out of the northwest, an easy 20 knots-plus with powerful gusts, on my port quarter. As I entered the confined basin, I discovered another boat in my assigned spot - apparently preparing to depart, but with captain and crew still saying their leisurely goodbyes to some folks on the dock, including the oblivious dockmaster.
With that much wind on the stern or beam, in that confined basin, stopping or turning around in a heavy, underpowered single-engined sailboat were not options. Spotting an open slip next to a finger dock slightly downwind of the face dock, I had no choice to bear off and go for it, even though:
1) It required tieing up port-side to, and
2) even though I was all rigged with fenders, lines, and inexperienced crew positioned to handle my intended starboard-side docking, and
3) even though I would be slowing and entering the slip in a howling crosswind with nothing to my lee except someone's expensive yacht snug in the adjacent slip, and
4) even though my boat, when backed hard, drew the stern to starboard (IOW, away from the finger pier and pilings I needed and toward the aforementioned neighbor), and
5) even though I really wanted to wake up and find this was all a bad dream.
Based on the dockmaster's advisory and instructions, delivered over the VHF ten minutes earlier, I had carefully thought-out my approach and docking maneuver, discussed it in advance with my crew, and had placed everything just where it would be needed. What I intended as a safe, no-drama docking in adverse conditions turned into what surely looked like amateur hour. No harm done, but it was pandemonium for about forty-five seconds while I directed my willing but confused crew to shift a couple of lines (leave the fenders where they were for the moment, I said). Hastily, nearly miraculously, someone got a forward spring line onto the second piling from the tip of the finger, and I was then able power the rest of the boat alongside against a merciless wind.
No tip for that dockmaster, I can tell you.