Longwinter 1 vs. Longwinter 2

The original icebox.

About five years ago I ran my first Longwinter sandbox (or rather "icebox") game with my Tolmin D&D group. We used a cobbled-together Microlite variant I assembled after giving up on 4th Edition. It was one of the most fun campaigns I ever had, a time-limited survival-horror game of dwindling resources and sudden death in the cold, frozen wilderness.

This year I've decided to revisit the setting with my current D&D group, the Golden Goats. I replicated part of the experience by lightly re-skinning 5th Edition to have everyone start at 3rd level and not proceed far beyond 5th level (WTF!). Right off the bat I ran into the fun experience of the icebox morphing into something weird and different.

The original Longwinter was a grim, slightly viking-infused slog of ice and snow, axes and crossbows among the long-rotted ruins of a formerly advanced civilization.

The new Longwinter game has quickly become a pseudo-slavic spaghetti-western romp of pistols and great swords in a gold-rush setting of jostling humanities plundering and rediscovering the leftovers of an alien civilization (Picnic at the Roadside, Stalker).

With bad jokes. Many, many bad jokes.

But that's just how different groups run, and it's great. However, I've also run into other interesting game design challenges.

1. Wilderness survival is not much fun with this group. Tracking details doesn't help and just gets in the way of the loose and silly game we usually run. I need to find a better mini-game for this than the list of loot and equipment and prices and space requirements D&D usually requires.
2. My original icebox (see above) was built before I had as much experience with this kind of game. It had A LOT of locations (I count around 29) and I'm discovering that's too much. I can't keep them all straight in my head, and I don't have the time to prepare them all. Not to mention, the players just aren't going to see most of them. Realistically, we do about 0.5 locations per session.

What's one to do?

Copper memorite being held back by descendant.