Except now with years of updates and content expansions there are so many items it's unrealistic to keep track of it all anymore.

This. It made sense in Flash isaac when there were maybe 100 items, but now in Repentance+ there are just too many to count with many items looking very similar to others. Not including vague trinkets and run ending decisions like devil deals.

Yeah i think it should be an option to turn off. And like at my most addicted I would say git gud. But I come back for a few runs every few years and while I can remember some bs like soy milk + libra breaks the game in your favor but soy milk + brimstone is fucking unplayable. There's so many items

To elaborate:

One of the foundational elements of Rogue and Roguelikes (that is so polarizing it isn't part of The Berlin Interpretation) is the idea of randomized and unknown item effects. It goes back to tabletop gaming where you would find a potion and have no idea what it does, so you would give a sample to a rat you keep in a cage or splash it on a goblin prisoner. For obvious reasons, that shit went away in favor of skill checks. But in game that manifested as, on every single run, keeping a notepad next to you to know what Red potions did on that play through.

The BoI items were very much in that vein. Theoretically you would memorize them over the course of runs and learn the synergies that helped you. In practice... ain't nobody had time for that shit.

But it is a design philosophy that wasn't uncommon for roguelites/likes of the era.

Yeah I got the impression that's how they intended for the game to be played. I've had a BoI app on my phone for years to get around this.

All of the updates and content expansions and so on and so forth have really made Isaac unmanageable in that regard. Throw in the fact that there are quite a few item drops that are objectively detrimental in basically every situation so that a not insignificant fraction of the item pool is just trash drops that nobody in their right mind would ever pick up, and it gets ridiculous quickly. Once you have enough unlocked that you're regularly getting runs down into the lower sub-basements of hell, unless you're an absolute guru the meta is literally just to meta. Know a couple of the game-breaking combinations off the top of your head and cross your fingers that you'll run across all of the components. Ignore all other risks.

This is in stark contrast to e.g. Dead Cells, which is why I've got such an immense respect for the latter. If you're willing to adjust your play style slightly, every single drop in Dead Cells is a viable weapon that can be deadly in the right hands. You could be wielding a legendary golden abyssal trident, sure, but you can also just as well beat the shit out of all the boss monsters with a pair of frying pans tied together with some rope. It must have taken an immense amount of work to get all of that even vaguely balanced and ensure that there were no duds, wheras Isaac's strategy seems to be more just throwing shit at the wall (probably literally...) to see what sticks, with a garnishing of deliberately adding things to troll the player for the lulz.

Same, I enjoyed the gameplay but every item drop was far less exciting because I'd need to pause and consult a wiki before making a choice.

That certainly was the intent. I just hated it. It felt like every run was doomed from the start until I managed to get through the seemingly endless number of runs that would be needed to suss out not just what every item did, but how they interacted. There were parts I really liked, but I kept putting it down because it just wasn't fun. Once that daunting requirement was removed, I had a blast and played it a ton. I haven't gone back to it in a long time and it still remains one of my most played games on Steam.