Sell the Beats earmuffs and pick up Superlux HD668B headphones for under $50.
Drop the Apple earbuds in the garbage and get TRN V80 in-ear-monitors for under $50. Add a pack of random eartips to figure out which ones are most comfortable for you.
Your MBP's built-in speakers have no bass below 160Hz or so, and bluetooth party speakers have all the sonic charm of a box of Kleenex. Spend $300 on a pair of JBL 305P powered speakers and plug anything into them -- they're a distinct upgrade from basically everything costing less and an awful lot of speakers costing twice as much.
Buy your music on CDs and spend the ten minutes per disc copying them. Do you know you can fit 1300 full CDs in a one terabyte disk without any compression at all? Or buy FLAC or any other non-lossy compression version. Buy directly from artists whenever possible: give them the best margins.
Use wires. Use headphone jacks. Use cheap ground loop isolators when you get hum from power lines -- they used to be really expensive, now they cost $10.
We live in a time of high-quality low-cost devices that play music much better than anything your parents could have bought without spending a month's grocery money.