No not really, only in some drastic instances. Like some audio uploaded to Youtube is either so low or over gained it's not even funny. Not to mention that the audio is already compressed to begin with, and Youtube compresses it further. Because cheaper speakers (like small bluetooth speakers, a lot of headphones etc) are low fidelity a lot of the quality you'd expect is missing so it's hard to tell the difference.
Yea I'm too cheap to pay for that. If I ever use a streaming service it's on my phone and Apple Music is already lossless (which I don't pay for lol)
That's adding an additional layer of compression or adjustment to the mix. Audio is just like images where the more you save, reupload, reedit, etc the more it loses quality. Same goes for video. You're taking an already compressed source, sending it through a DAC, which is going through another DAC, to your speakers. In MOST cases, it's hard to tell the difference between an MP3 at 320 and a 24bit FLAC file raw.
Here's my speaker setup for my gaming rigs.