For the longest time, I shared this hobby with my dad. He would find the good deals, buy the games, then he and I would spend the time together fixing them up and playing them.
Then around the time I was a senior in high school, 17 or so, I started making my own money in a significant way (relatively speaking), and purchased my first game: Firepower for $300. In hindsight, I definitely overpaid for that nonworking basketcase, but I was so excited to have a game with multiball, since all my games before it were EMs.
When I look at my collection now, versus then, and how excited I was to have a single game with little features like multiball and an attract mode (I used to think that was so cool), it's humbling how far I've come.