Dunno if I go actively searching for difficult music, so I may not have the best answer for that specifically, but here are 5 albums I consider hidden gems or underappreciated:

Horse Bitch - RIP Pistachio

Tattle Tale - Sew True

Gaytheist - The Mustache Stays

Codefendants - This Is Crime Wave

Irist - Gloria (actually an EP, if you'll allow it).

These probably won't take you 5+ listens to appreciate, but I do think they're smaller releases worthy of greater attention. Hopefully that's close enough for you. ✌️

I truly wonder where in my post I implied that I am drawing significant conclusions without giving something a good few listens. Again, I think you are making assumptions of my listening habits based on severly limited information presented to you.

No, I think you’re absolutely right and it’s comforting to know there are others who do this too. I have a kind of 3-5-7 trial period for getting into new music. If it’s crap but I want to give it a chance, I’ll do 3-5 album plays; if it’s ok but has potential I might not see, 5-7 plays. Anything challenging but enjoyable gets minimum 10 plays.

About the self inducement, that is making me question myself a little. There are things that I’ve tried over and over to get into that I just cannot no matter what, but I’m seriously questioning if it really is possible to “make” yourself like something through type of, I guess familiarity?