My personal approach is to get all the basics down, source (first and always), amplification, headphone/speakers. (Just use the cables that come with the equipment.) Then, add cables to the mix to see if you observe a difference. I've heard significant (positive) differences paring kilo-buck cables with very inexpensive products (e.g. the HT Magic Link II and the uDAC is surprisingly killer), but only if you already have the cable inventory. It doesn't seem practical to buy an expensive cable without a good foundation. Again, that's just my personal approach and 40+ years of experience in music and music reproduction.
Also, there's a lot of good experience to be gained by doing things in phases, gradually. Experimenting can be fun. I was pleasantly surprised to find that clean AC made a significant difference, as I was with maintaining clean connectors (via Caig), and later, cables, even inexpensive ones. Sometimes the effect is cumulative. Once the bug bites, it's hard to go back
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