When I was 9, in 1993, I hurt my eye and couldn't go to school for a week while it was healing. To make it bearable, my dad somehow got me a pirated copy of the secret of monkey island from a coworker (he worked at a PR company so I still find that mildly surprising today). The game had a copy protection feature where there was a spinning wheel and you had to input some text that was revealed when you combined the top of a pirate's head with the bottom of a different pirate's head (IIRC). This was defeated by the office photocopier.
Eventually I got stuck on a puzzle that I just couldn't figure out. Rather than giving up, I sent a physical letter through the USPS to Lucasarts explaining where I was stuck and asking for help. A few weeks later, I received a response with Lucasarts letterhead with the solution to the puzzle. I actually ended up sending two or three letters to finally complete the game. Talk about a different time and place.
Of course a few years later I racked up $30 in hint line charges while making my way through Sam and Max Hit the Road. It took a lot of chores to pay my mom back for that.