I used a Zune and synced all my music at school as a guest device, and there was no way for me to rip dicsographies to flac and had no hardware to play them.
The main way I got all my files back then, that you haven't listed here, was by googling the name of the album or song I wanted followed by either .zip or .mp3 and then the words mediafire, megaupload, or beemp3. "[album name].zip mediafire" this was when googles search bar features still worked and exposed most of the raw index (100s of result pages. Goooooooooooooooooooooooooooooooogle)
Only if I couldn't find it that way would I then resort to using "N°1 Free online Video Converter" onlinevideoconverter.com to rip a song from YouTube. That was usually reserved for meme songs like covers, the Ultimate showdown, Epic Rap Battles, and stuff like the Bedroom Intruder autotune and other Gregory Brothers viral hits.
My golden child older brother who was a way bigger intellectual (not technological) nerd than me was the one who begged for the credit card to buy songs once napster shut down. He wouldn't always buy from iTunes, sometimes he would "save money" by buying them for pennies on the dollar (like 20 rubles) from a Russian piracy site that purported to pay the artists, as though that gave him the moral high ground over my piracy, when it was obvious there was no way that was happening.