Was in a tight anchorage when an engineless boat came in under sail and tried to anchor among others... the lone sailor let out the anchor, but didn't drop sail quickly enough after heading up. The boat fell off into a reach while the skipper was trying to rush back from the bow to drop sail: The boat accelerated quickly and rammed bow-on into a pristine power boat (definitely a high-end build, easily a $500k+ boat) and cracked the hull-deck joint area around the mid-section. The sailor had no insurance.

Even if you have the skill to do it successfully 20 times there will always be a time when things go awry. For that reason I think it's reckless and irresponsible if you don't make every effort to reduce risk in a tight spot. Risk is smaller with light-maneuverable sailing dinghies or areas where other boats aren't close, or larger boats with engines on and sails down. It's all about control and weighing the consequences if things don't work out as planned.