Do you regret how much money you've spent on games or in game items/currency?

Yes, mostly when you invest and the game either stops updating or goes offline. I loved the Marvel Heroes style Diablo game from a few years back (mega whale in that game). I cut back in the last year, not even realizing it was getting canceled. I'm happy I didn't spend too much right before that (I got annoyed when they started only updating the console version). I do find any money in Overwatch wasn't worth it. The cosmetics were never that special.