I don't think the "reward feeling" for losing at a video game is the same thing as what our "Inner Bruce" goes after. They may be related, I don't know. But losing as a video game can be fun, more than losing in real life. Fun in the same way the rest of the game is fun, it's not a special kind of fun.

I get that a lot in Spelunky, where you often make a small mistake and splat blood flies and you have to start over again. but it can be fun.

That's an important distinction between hardcore and casual games. Some players don't mind getting killed horribly and having to start over again - it's what they expect. But other players will be discouraged and feel bad if the game tells them that they suck. That's why most casual games are very nice to the player, and often you just can't lose at all. A decade or two ago, the game industry was mostly focused on hardcore players; recently they have found out you can make a lot of money with casual games (targetting "middle aged women"), but you have to make the games differently.

Maybe it's because hardcore players expect to die over and over in video games, and they know viscerally that it doesn't matter at all, so when they lose, they don't have any negative associations. On the other hand, new players haven't made that dissociation, and feel bad about losing.

I never thought much about the relationship between "self-sabotaging to lose in real life" and "enjoying losing in video games", it's interesting ...