In the rain, not knowing how to operate the bilge pump (or that it even existed as an option) and running the boat almost vertical with water in the bilge, like it was an amusement park ride. Did this on 2 trips until I decided to read online about the cause of this. Eureka!
Not knowing how to read channel markers and deciding to go "as far from red as possible" and banging the prop in some rocks, on my second trip out with the new boat
Not knowing how to read hazard markers and riding straight into a rock (and denting the hull)
Forgetting the hull drain plug and riding around the lake for 20 minutes wondering why the boat won't get on plane (and cursing myself for having added too much weight to the transom as I thought that was the culprit) - took about 30 minutes to drain the bilge once I got it back to the ramp and on the rails
Couldn't for the life of me get the engine started while on the lake. Got freaked out that the engine was dead until I realized that the kill switch has to be in the "on" position and the drive gear in "neutral"
Disassembling the Sonar unit at night before returning to the ramp and running without a depth finder, right into some rocks (had no idea how shallow I was) - I see a theme here...
Forgetting to charge the batteries, ghetto charged them at the ramp with a handheld charger and my truck. A few hours later, ended up getting stranded on the lake with a dead battery and getting towed back to the ramp by a pontoon.
Got my fishing line stuck the trolling motor and while I was untangling the mess, washed away to shore into some rocks and broke my transom transducer
Got really mad at Bass Pro because my trolling motor wasn't working after getting the boat out of storage. I undid the front slat of the deck to check the wiring, only to realize 30 minutes later that the motor was in the "off" position (I forgot that there was an on/off switch).
Drove for 30 minutes with the trailer coupler lock in the "up" position
Had trouble getting the boat on the trailer and had to "walk on the trailer" to the back of it to grab the boat - slipped and fell so hard and scraped my leg so badly that I thought about hiring a personal injury lawyer (joke)
Fished a high profile tournament (100+ boats) with my brother (who had never driven the truck nor the boat) - Backed my bro down the ramp in the boat at 4:30 AM amidst a really long line of boats and spectators. My bro didn't know how to turn on the nav lights nor the boat (although we rehearsed, he got flustered and forgot). He flipped every switch he could get his hands on (bilge, livewell, horn, etc.), was finally able to turn on the ignition and ran into another boat
Threw the anchor down without it being tethered to the rope. Bye bye anchor
Tried to park the boat with the wind at our dock. Hit it so hard that I almost tore it up. Twice.
My bro tried to toss a life jacket to me from another boat. He tossed it short, it fell in the water and it auto-deployed (at least that mechanism works, I guess)