The first year is probably the hardest.
I've owned my boat for 23 years and developed a system for most tasks. I can winterize the engine, the air conditioner and the two sinks in an hour and strip all the linens and extra clothing and remove all liguids in another hour, wetvac the bilge and set the cushions on edge and open every locker so air flows through, for the winter in another hour. I remove all liguids so they don't sweat in the cabin. This year, the yard guys blocked my boat at 8am and I was driving home at 11am. I'm not bragging. Many others are quicker. I leave a couple jugs of water in the cockpit so I can make coffee when I visit the boat over the winter. I have a 2 1/2 hr drive home, so I keep checklists in my phone and use them so I don't forget something.
Pictures. A new challenge for me is my comcast email won't let me send photos anymore. Gmail will accept some but not all, and I started using a cable to sync my phone to the laptop. I guess I am being forced to use the cloud or something which I'll have to learn.
I attached some pictures of my boat from this summer. I hope it spurs others to share some photos.
Chuck S