It takes 20-30 minutes for 1 year, so 200+ hours of play time. This was maybe my third game played 1½ years ago when I got the game and found out that as long as you didn't divide the plunder after you were 40 or so you could keep going. I thought you would continue to age as time went by, but you stop aging when you reach retirement age which differs depending on the difficulty level. Once I had finished all the quests I just wanted to see how far I could go with it, and used it mostly to test new skins I had made. A few of these are available for download in the mod database at Hooked on Pirates.