How do you keep your seldom used equipment in proper running order?

I have a basement work bench, a garage, a truck, and a barn. They all have a supply of tools so I can readily work on things when and where I need. Hand tools work forever. Those are easy. But I invariably have problems with things like flashlights, battery operated drills, generators, mowers, tractors, chain saws, etc.
I (almost) always put things away nicely so they will be ready, but they never are.
Here’s an example. I just went out to use my chain saw, last used about a year ago. I gassed it and noticed the bar oil has leaked out. I grab a flashlight, conveniently attached magnetically to the barn door, so I can see where to pour, but the flashlight batteries are dead. The voltmeter I keep in the barn also has a dead battery. So now I need to fix my voltmeter, and my flashlight so I can put bar oil in the saw.
This seems to happen all the time. I go to use the push mower and the gas cap won’t come off. I use pliers and the cap breaks. So now I have to make a work around. I go to use my electric drill and the batteries are dead.

It seems like I am (to quote the comic “Pickles”) walking around “but first.” I need to mow, but first, I must fix the gas cap. But first, I must charge the drill. But first I need to find my glasses. But first…

How do you manage to keep all your stuff working? Do you set aside a day every month or two to recharge and service everything? Do you just fix everything as it needs?