I guess I'm not very picky (by audiophile standards). I appreciate quality, but I can also appreciate being 98% of the way there. For home listening, I'd be pretty much entirely happy with just my Sennheisers, a parametric EQ to fill in their bass and make a couple other tweaks, and a respectable-quality laptop headphone out (and I would listen that setup over literally any other headphone setup without PEQ - it's simply essential for headphones IMO).

Past that, it's the land of extremely marginal improvements and consumerism for consumerism's sake. I have much fancier stuff and like trying new fancy stuff, but if I'm being perfectly honest with myself, it's a waste of money chasing ultimately meaningless differences and marginal improvements. But it's fun, so...