To be fair trial and error and RNG are just par for the course with classic roguelikes, but learning how to manage all that is part of the appeal. Nethack and Dungeon Crawl Stone Soup are probably the two best-supported old classic roguelikes out there. Honorable mentions for Dwarf Fortress, which basically abandoned its roguelike mode in favor of a fortress simulator, and UnReal world, which is a weird outdoor primitive survival game that's a testament to one man's obsession.
There are also more modern offerings like Tales of Maj'Eyal, Caves of QUD, and Dungeons of Dredmor that are fully faithful roguelikes with either more modern graphics or QOL upgrades.
I discovered Shaun this year and binged most of his videos. The War On Science was this year and is great, though 4+ hours is a big commitment... Most of his other stuff is shorter.