If its any comfort, I recently observed a captain try to dock his beautiful Passport 44 in a fairly easy slip. He is not new to sailing, I think this is his third yacht. He claimed a fouled prop (likely from what we are seeing in the Chesapeake this year) but what I observed was poor judgement and bad approach. He end up being pushed by the breeze down the fairway to the bulkhead slips, then bumping off a few pilings and boats (no significant damage occurred to my knowledge other than a bow light) trying to go stern first into the slip. Ultimately he went out the fairway and decided to come into the slip bow first, after two attempts he made it with some help from a couple of us on the dock. It wasn't pretty, embarrassing perhaps, avoidable? Probably. Felt bad for the guy because the whole marina was watching.
On another note...recently we were in OBX and we went down to Oregon Inlet to see the catch come in from the big deep sea fishing boats. Damn, I was so impressed in how they maneuver these big sport fishing yachts. I have never seen anything like it, they back into these slips fast! I mean FAST!!! Yea sure, twin screws and HP make it a lot easier, but these guys are serious pros! The catch was impressive, their boat handling skills blew me away!