As for my picks I would recommend

Beginner IEM I would honestly first play around with the different sound signatures with sets that are sub $50 first and once you find what you like make the appropriate upgrade. For example Mele -> IKKO OH 10 7hz Zero -> Kato

Headphones: I would recommend starting out with the SHP9500 then upgrading to the Sundara ( I owned the hd650 and hd600s and wasn't a fan of the Sennheiser veil; I also wanted better technicalities)

Speakers: It depends on your preference to go for a powered or passive system. For now I would recommend the Kanto Yu 4 with a decent subwoofer.