@kelbot
This feels like a question for me! I like building myself frankensteined audio set-ups made of old review hardware, random second hand stuff, things my friends and I found in skips, and a couple of actually decent things I bought with money.
I have a Rega Planar 1, an ex-professional Sony cassette deck (cost: 1€ from a local wedding venue that went digital!) and an Onkyo CD player hooked up to a (recapped) Leak Delta 30 (it's a transistor amp from ~1970), hooked up to a pair of Jamo tower speakers.
Unfortunately, I need to clean up the contacts and tracks on the Leak and take a stern look at the speakers, because I'm having issues with the left channel. When I see a nice and cheap set of second hand hi-fi speakers, I'll switch the Jamos into my home cinema setup, though. (Currently an Onkio AV receiver hooked up to an M-Cube 5.1 speaker system.)
For day to day digital file listening from my workstation, I have an AudioQuest DragonFly DAC hooked up to a pair of old Mackie CR3 mini monitor speakers (they're better than they deserve to be for the price). I used to have a pair of Behringer Truth B2030A monitors in my old office, which were better, but they're too big for my current setup - I might put them back when I re-integrate my audio production gear with this system though.
I just play tracks through Clementine because, although I'm sure I could do better, I'm lazy.
I'm a huge fan of dedicated MP3 players, but I don't have one right now. I might build one, but DAC modules add so much bulk in DIY that I'm not sure how to make the mathematics of size/quality/cost work out.
looks at essay
I'm going to shut up now.