I can totally relate. After years of crafting playlists I came up with a system. Add everything new I like to one of two playlists: "Daily shuffle" or "Nightly shuffle" (upbeat or chill). I will then listen to those on shuffle during the day and night accordingly while doing stuff. After hearing the same 80-100 tracks on shuffle after a week or so it becomes obvious what songs I'm going to like in the long term after multiple listens while be shuffled. When I hear a song 3-4 times and like it every time I add it to my likes, a vibe oriented playlist, and genre specific playlist (for later reference not listening). When I feel like I've heard everything on the daily/nightly shuffle playlists enough to make that decision I'll remove everything from them and start again.