I think I've got it. Something called AMP-SUPERSEAL, which I gather is widely used in cars and consequently super-cheap online. You can even get all kinds of rubber housings for it if you want to get extreme, but the basic 2-pole unit looks like enough for me. I know that the ciggie plug thing can be made to work, but it's partly an aesthetic thing and partly size. We sometimes go tent camping on the Dutch coast in my little Alfa Romeo wagon, and we number five including the Au Pair. The glove box in that car is exactly what it says - just big enough for some gloves and a few maps! Get a bigger car? Sure, but my parking spot in central Cologne is just big enough for the car I have, and I'd rather drive an Alfa than almost anything else with four doors.
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That looks like a very good solution for you.
A vehicle battery can be either the source or the load (for a charger) so I like genderless Andersons for connections I'd make with both hands while parked, such as a battery charger or winch. Then the charger's outlet mates with the portable cooler's inlet to precool it at home and either can connect to the battery. A DC power meter which reads current in only one direction can be plugged in between them either way, to measure charge or discharge.
I added a lighter outlet with a cover instead of an Anderson to the tractor to plug in the flasher because mowing fills everything with dust, and I plug in the flasher with one hand while driving. I have to be careful using the outlet to charge the battery because the male lighter plug would be hot on two exposed terminals if connected to the charger first.
-jsw