Monster Hunter isn't exactly fun to lose, except if you're playing with friends who will tease you for having to ride the Kitty Cart back to safety. With that said, I want someone to try telling me that Monster Hunter isn't fun, even with grinding for materials (FWIW, the games have gotten less grind-y with each iteration in my experience), and even with calling the newest game by its true name: Hit It Until It Dies: Generations.
When you're killed by a monster, there's anywhere between a handful or swath of reasons why you died. Armor's not good enough, unless you're a gunner, in which case your armor will never be good enough. Mistimed block/dodge. Too aggressive and got caught in a slow animation. Mistimed deployment of items (drank a potion just as Stygian Zinogre was coming out of its slow walk and targets you). Whiffed on a few attacks, allowing the monster to get into a better position to attack (particularly true for Hammer/Hunting Horn, where missing the head means missing KOs and failing to create openings for your team).
When not hunting specific monsters needed to rank up in the Guild, you're usually seeking ways to gain an edge over those key monsters. This usually involves getting better weapons and armor, more items (incl. things to create openings such as flashbangs and paralysis knives), better ingredients for meals that give you buffs for the hunt (which only last until you die the first time), the works. However, even with all of this shit, unless you're fighting High-Rank monsters after grinding with your G-Rank friend (AKA cheating), victory is never assured. Personally, I think that's what makes up for games that aren't fun to lose: the requirement of the player to achieve victory for himself/herself.
Of course, as mentioned earlier in the thread, if the game is fun to play, then whether or not it's fun to lose isn't important.
