IMHO, everyone should be able to sail into/out of their slip. I was always taught that there are 3 engines on a boat, 2 up high and the iron genny below, and knowing how to fully utilize each both together and independently was the sign of good seamanship. Our club used to not allow folks to sail into their slips but after having members crash land with their motors more often than with their sails we changed the rules. Now we teach a course on how to sail into and out of a slip so that everyone knows how.
Watching the video , I understand the practice runs. Having had to dock a 20 ton boat at the fuel dock in Berkley with no engine, you learn very quickly that being able to dock under sail when the engine died is a skill everyone should have. Heavy air just means things happen faster but if you notice he had lots of help, practiced so he understood what was going to happen and then committed to the run. Nice sailing, and excellent boat handling. Throwing a line and trying to haul the boat in would have put at least one or two people in the water, if you could catch the line and, in my opinion would have been much more dangerous. The video makes it look like he came close to hitting his neighbor but I bet if you were up close you would be able to see that he never really got close.
By the way stopping a 20 ton Hyalis at the fuel dock under sail and getting to parade off onto the replacement boat while everyone watched was fun!!.
Not reckless, just good sailing.