Terrible win rate with Caro Kann

That's fair, but I'm hoping to get a better understanding of the game as to WHY it's not working

The basic flow of a game is bring your pieces off the back rank, castle, play a pawn break, then infiltrate to your opponent's side of the board.

In the caro you usually have this structure:

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So your pawn break is either e5 or c5. If you can't find a way to play one of those breaks then your position is just worse... but you can't play them right away. Pawn breaks favor the side who is ahead in development, so first you'll get all your minor pieces off the back rank and castle. Then you'll play e5 or c5 at a moment when it doesn't lose material.

That covers what might go wrong for you regarding the opening... if you're doing those things but still losing then it probably has nothing to do with the opening. It probably has to do with basic tactics and calculation.

For example this game

(See the variation on move 5 for what I recommend)

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This game by you used that sort of development. I think that's a big improvement.

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Oh, you're white in that 2nd game, I didn't notice lol

Thank you very much though, that was very helpful.

No problem.

And if you look with the engine, 5...a6 runs into trouble if white plays very aggressively with g4, f4... but I assume your opponents aren't going to play the first 8 moves perfectly and super aggressively like that

But if it bothers you, then you can skip 5...a6 and just play the same idea with 5...c5 right away. a6 is a little safer (and has been played by a few good players in the past) and if your opponents punish you for it it's easy enough to just skip it... that's the reasoning behind why I recommended it.

Here are some famous games with it: Tal - Botvinnik
https://www.chessgames.com/perl/chessgame?gid=1032564
https://www.chessgames.com/perl/chessgame?gid=1032566