dcpigpen

Vagyrisk Claws from the original FF7. For starters, the enemy that they can be stolen from only appear in a small area on the world map, where other enemies also spawn. Add to that the fact that most times you try to steal it, you get a Soft instead. On top of this, your chance of stealing it goes down the higher your level, and it actually becomes impossible to get after a certain point. If you want to steal 99 of them, you're in for a time. Other than that, getting a gold Chocobo with the best stats possible means racing A LOT. I still here the Chocobo Square music in my nightmares sometimes.

Gambler 10 is easy if you can get to it before the mission "A Fine Night of Debauchery". You are scripted to win the last two hands of poker in that mission, so just save the game afterwards and then you only need to reload until you win one more.

My current playthrough, I will quit and reload if I ever die, fail a mission, or get less than gold medal on any mission. It's not necessarily to make the game harder, it's more to maintain immersion.