How do you rationalize audio upgrades?

There is, gentle readers, a hierarchy of audio systems. What that means is that with careful tweaking a modest cost system can outperform a more expensive untweaked system. And if you tweak the more expensive system you can potentially outperform an untweaked very expensive system. The degree to which a tweaked system can outperform a more expensive system depends on the effectiveness of the particular tweaks involved and the number of tweaks involved. Necessity is the Mother of Invention. You only need to know where you want to go and how to go about getting there. 

@geoffkait  I thought all roads led to the Sony Walkman via the Cassette Tape byway?

You only need to know where you want to go

Already memorized. : )     

I’m looking for the tape version of this... : )

https://www.teeshirtpalace.com/products/i-am-your-father-retro-floppy-disk-usb-t-shirt?sku=IAF20526-SPORTGREY-1-AT&gclid=CjwKCAjw0vTtBRBREiwA3URt7nvghKqZJbFfEubgc1FZY44UJrr2NdomaHoCPoluZLAEcgASqHtFcxoC8rEQAvD_BwE

Here you go (or something similar):  [Never Forget]  : )

https://www.spreadshirt.com/shop/design/never+forget+floppy+disk+vhs+and+casette+tape+mens+t-shirt-D5aca13e7aa0c6d3a4b92cfd0?sellable=rAq2138LQ4cgn727Xo20-210-7&affiliateId=7555&gclid=CjwKCAjw0vTtBRBREiwA3URt7rVl1xIB9Q5YJYlwgp5U3wDkxnEYSX7v2vmHvspQI5zTgaL6m7O8VxoCKUMQAvD_BwE

To my way of thinking, an upgrade has to do one of two things in order to be rationalized/justified....add an improvement compared to what you already have or eliminate a negative that is just eating away at you.  99% of the time, these will be sonic/musical in nature...but every now and then, aesthetics may come into play.

Oh...and one final thing...whatever change is being contemplated should not result in seriously reducing other important aspects of your life.