And also, I love to optimize things, so it made no sense to me why squeezing 1-2 more words in the track title would inflate the file size by 4KB. As a teenager, I probably had more time on my hands back then.
Ain't this the reason why most of us ended up here :)
Think about it, if transparency guarantees applied for lossy transcodes, you could encode mp3 -> mp3 thousands for times with no generational loss. This clearly isn't possible.
Of course, you could rip all your files again in a better codec, but the time required to do that is pretty intense.
That's not really a counterexample for the idea that one pass of lossy -> lossy reencoding doesn't necessarily mean certain doom for audio quality.