Can't decide if I should upgrade my Chu II or try out some planars 😞

Thinking of either upgrading to Moondrop Lan or Simgot EW300 or trying out planars with Artti T10 or Sgor Luna.

Each piece is around 40 dollars except for Luna, that I can get my hands on for only 20$, so that means I can buy some eartips and a DAC. Speaking of DAC, I heard planars heavily rely on those whistles since they use more power, but I am still unsure if it's necessary. I have a CX31993 and wondering if it's enough for those, since I saw some people suggest getting a 4.4mm cable.