What's your favorite "I regret buying this (later) I made the right choice" purchase?

In regards to video games as it seems you are focusing on, that's a tough one. I am very selective with video game purchases since due to their higher prices, it could very well have been a waste of $50. I guess it could be the first God of War which I bought a few years ago when I decided to add more games to my retro collection. I never regretted buying it first, but I was hesitant because I have never been into hack&slash games. The main reason I decided to give it a shot was because of my interest in Ancient Greece and Greek mythology. It was totally worth it and I ended up continuing on to the rest of series.

In regards to non video game related purchases, it would definitely have to be when, as an investor of precious metals, I went from 1st grade to junior high by skipping gold and going from silver to platinum. Silver is considered the precious metal of choice for beginner investors since it is cheaper but still has value and can rise at any moment. The next level up would be gold and after that is platinum. I don't why I decided to purchase $2200 of platinum rounds (collectible coins) at the time, but I did and two months before a spike in the value of platinum. I made of profit of $800. Rounds, of any precious metal, are considered more valuable than plain bullion bars because they are collectibles rather than just a bar. Being a collectible coin adds value since it is more desirable to a wider variety of people than just a plain bar which serves no purpose in a display.

Nothing. I never regret or doubt my choices, for at that moment in time it was the absolute right choice I could make.