How cheap can you go and still be happy with the sound?

For me:

A balmy, early summer’s eve,

My favorite chair on the back deck,

A Sony Walkman CD player (used) - about $20,

A pair of 30 yr. old Bose headphones - $100 (back in 1990),

A six-pack of beer - about $8 including tax

I had a pair of Sony sscs5 speakers for the deck (bought for ~80 dollars on a amazon sale). It was... meh ok. I put the GR research upgrade kit in it, ~300 dollars and it has become a creator of happiness.

Can't do the liquor anymore... but, the Sony does work well with the coffee/cigars on my deck. 

A six-pack of beer - about $8 including tax

I don't that exists in my town. Maybe for $11

I found that the dirtier and nastier the task, the more forgiving I am of flaws in audio quality.  Listening to music while cleaning the bugs off the motorhome, for example, does not require a pristine delivery of an audio masterpiece to be a beneficial musical contribution..  Just something more pleasant than standing on a ladder while removing bug guts gets a "pass."  Working on a classic car?  Same rules apply, but  genre also matters.  The laid back sound of California surfer music instrumentals lowers the stress level and reduces the "tool throwing factor" by 50%.

Here's my home office system under $50:

B&W C201i -- $10 

Onkyo R1 amp -- $ 10

Sony 300-CD changer -- $5

Realistic Lab 430 turntable -- $20

It's mostly used for background music

@waytoomuchstuff... +’something significant’...;)

When banging the rocks together to improve and/or creating (some may say ’cretin-nating’, but they just don’t....."....well, never mind...").

’Something pleasant to move the task along’ covers a lot of my need and desire for ’decent audio’, when involved in a non-audio ’fo-cussed foray’....

DLH ( ’Difficult Listening Hour(s)’ ) is when you’re ready to ’git down ’n In To’ that which taps your toes is a whole different activity....

...esp. when you’re rubbing your forehead from that launched wrench that bounced off a surface and returned with a vengeance....

True story, that....wrenching on a Triumph Spitfire with a cantankerous bolt....

I pick my unintended targets more carefully since...like the object itself v. random uninvolved.... ;)