I also like this idea. I don't have a problem with being meticulous; I enjoy making this game and its main purpose was just to keep me busy and thinking, anyway. The primary issue I can foresee with this, though, is that my game is open-world, so the player has access to a lot of stuff after a certain point, and thus it becomes more difficult to balance. However, as it's mostly side stuff, I don't want to create encounters that expect the player to have the most optimized equipment, as they might only have one save and be in a position where they can't back out. It'll likely be an ongoing process for me.
Here's the fun part. My game is "Open World" as well. It was the only viable way I found to make sure "balance" was remotely preserved.
But, I'll address your concern here too, because I already solved that problem in my particular project. I don't know if it'll help you, but maybe it'll inspire your own idea.
As you "move forward" in the game, you are going to have "guaranteed equipment" and "guaranteed stats". There's no reason to continue testing out the first weapons you obtain in the game at level 30, unless your gear progression is virtually non-existent. Your list will be immense if you keep trying to use "all equipment available up to this point". At some point, you need to whittle it down to the guaranteed equipment you'd have up to that point and all the "new gear" you'd have. A player is going to equip anything new they run across, whether they get it from a quest or from a chest.
It's easy enough to check for "bare minimums" if you study your own map design a little. If a player does zero sidequests and only takes the routes through your map that get them to the main quest stuff, what will they have? If they hit a town, list the equipment in the last town they hit before the location, that'll be pretty close for the "bare minimum". Are there chests along the way with equipment in them? List those too. Always assume that while a player might skip all your sidequest content and skip exploring... If they see a chest on screen, it triggers a part of our brain that makes us want to go get it. So, any chest the player can see on screen on that route, you include its contents as well. Unless it is impossible to obtain the first time they see it. Do monsters drop equipment? List those drops as well. These are your "bare minimums" table. This is the equipment most players are likely to have on hand, regardless of their skill level or experience with an RPG.
As for the rest of the equipment? No need to check every single solitary piece of equipment either. What's the best stuff they have access to by the time they reach this point of the map, or this quest, or this story step? If they went out of their way to find it, what's the best they could have? Then, you just average the "best" against the "bare minimum" for where your difficulty should likely be. Just figure out where on that curve you want the challenge to be. Let players be under that "optimized" position. It's okay if people fail to do your content and thus suffer a little from it. There's no reason to hold their hands. It is also okay to have players be above that "optimized" position. Obviously, you don't want the vast majority of players above what you've determined as "optimized", but it's okay to have roughly 20% of players or so to be above that curve. Keeping that curve where you want it is just going to be a bit of balancing your equipment, your skills, your states, and enemy stats. Which... Not too difficult to do if you've got time to Battle Test.
As for getting stuck... Eh, design something like an "Escape Rope" from Pokémon that automatically lets you leave a dungeon. Or, create an item that lets you avoid combat if it's equipped. There's a few anti-frustration features that already exist in RPGs. If you're worried about it, just put one of them in your game. You could maybe even make it an item that consumes a percentage of your currency in exchange for the escape back to town. That way, players wouldn't spam it as a teleportation tool, and they'd instead have to actually be in a tight spot to consider using it.
