I do the exact same thing with 人数. 人性 and 人性 are probably my biggest recurring mix-up. Half the time I’ll switch the readings for 人. As for meaning, it’s a free for all between “character” “personality” “human instinct” “humanity” and an endless variation of other things that aren’t the answer. At this point I don’t try to think about the right answer anymore, I just put anything in and get on with it. I also get 転ぶ and 転がる wrong a lot.
A few have readings that only come up in one or two vocab words. I tend to get these right a lot in Guru, but after they’ve been in Master/Enlightened I forget when they come back. Includes things like 人形, 名字 and 計画.
I assume a lot of this stuff will start getting falling into place once I begin encountering them “in the wild” so I don’t worry too much about it, I’m still just starting out.
EDIT: Oh god and all the “one’s wish” “heart’s desire” “wish” “hope” “request” I’ve given up on as well.