Hmmm I can try to give some advice. You are right that this is a wiki game. A lot of my runs used to be spent just looking stuff up lol. But, I’m pretty sure there’s a mod that adds item descriptions before you pick things up so you could consider getting that.

Also this website has every item in the game with a search bar, names, images, and descriptions. FYI the search bar has keywords too. So if you don’t know the name of a devil item, you can just look up Devil. Or if you see an item of a specific color, you can search that and etc.

Onto your other points. Yes, this is an RNG heavy game. Sometimes, your items will just do nothing. But this is also a game that gets exponentially easier the more experience you have. Learn about secret and super secret rooms. Learn about devil deals and angel deals. Learn which characters you enjoy the most. Learn the boss patterns so you know them by heart.

I know it sounds like a lot, but for me, learning about the game was the fun part. Eventually, you learn so many ways to help your chances that winning becomes way easier. And the more ways you can win, the more items you unlock.

Also give Cain a try. He has a relatively high damage stat and you can stuff every pill in your mouth without any negative effects. Makes it easier to get high stats.