The contents of these two lockers never leave the boat.
That's the only way to do it IMO.
When something is used, you make a note of that and replace it asap.
We've done the same thing with camping gear.
All we have to do is load 3 plastic totes in the car, along with the tent+coleman stove+cooler, and we know it's all there. Makes it very fast to load up and go.
This time we took the "kitchen" camping tote with us, but the boat will have it's own forks, tongs, etc. next season.
The funny part about not being able to find those clevis pins... is that once we had launched and I started sorting thought things, we found the Clevis pins had escaped into bottom of the starboard locker under the settee.
I have 2 parts organizers with hardware, 2 tool boxes with other supplies and tools, and one of those big all-in-one tool kits in the port locker under aft table seat.
I have to get better parts organizers, the lid on these 2 aren't 100% tight, so small items call fall out. The latches are junk.
The lockers under the table seats aren't "sealed" at the bottom (unlike the starboard one), which would allow small parts to end up in the bilge if a container opened up.
The truck has 2 box tool boxes, one of which various things including 2 trailer wheel bearing kits packed in grease in plastic zip bags.
Eventually I'll weld a trailer jack on either side of the trailer, to enable trailer tire swap/repair, without needing to carry the floor jack I use now.
To minimize the tools, I plan on eventually doing an inventory of tools needed, and making up a smaller kit.
The kit I have on the boat now, has over 300 items and is overkill. It will be moved back into the truck, once I plan my optimized boat toolbox.
The good thing is, most sailors have a hardware kit, so I was fairly confident that we would successfully borrow Clevis pins.
It's nice to be in a marina that is specifically intended for sailboats.
We drove up to the lake around noon yesterday, and actually took her out under sail.
It built up to 16 knots, with short choppy waves, and the occasional bigger ones requiring "steering" through them to minimize roll. The admiral was feeling seasick by the time we got back to the marina, and I wasn't too far behind her. Shallow + Huge =lake is more often that not, uncomfortable and even very nasty
I'm making up a list of remaining tasks, and observations, and will post it once compiled.
I was making notes as we sorted through gear, and after we got back from sailing yesterday.
Hopefully it will help others.
Cheers !