For me this one's a little tough (especially with me being more of a 'mutual' fan, but for this topic I'm gonna curb that bias of mine for a while), because as you said both versions have their value. I guess with me, when I'm playing as my faves girls in a fighting game, I think I wind up clicking a bit more in situations with me losing to someone that's stronger than me than the other way around. I like to think of my skill of playing games to be a bit higher than average, so I sorta paint that onto my girl characters' styles when I play; being confident in any given battle and willing to compete and show off their skills (and looks as well). Knowing their stuff, they tend to win quite a bit, which builds their confidence going from battle to battle, and even if it's a loss, if it's close, then it's not too bad... They take the battle as experience and try to do better next battle...
...Which makes it more surprising when out of nowhere [Tekken example] a King enters the ring and suddenly my Xiaoyu or my Lili gets grabbed out of every one of their elegant maneuvers and attack, getting slammed all around the arena or [Street Fighter example] a Mika or Nash player dominates my Sakura or Chun-Li... or [BlazBlue example] a Tager or Terumi utterly demolish my Noel or Mai. It's just so sudden to go from competent to utterly dominated despite holding your own in most battles, and a big feeling of helpnessless and weakness overwhelms them. Suddenly, you secondguess your abilities... you don't know what to do... you feel utterly exposed, all the while she's being beaten up with no way to stop it from happening..., then all of those feelings turn into humiliation and ultimately defeat. That opponent was completely out of your league, and he or she showed it by whooping on you so much you can no longer stand and fight back. For all your training up until that point, in the end, it didn't mean anything and you lost; badly... leaving you open for the victor to gloat over your weakness and embarrass you further... Nina stepping on Xiaoyu's back as she's face down on the ground... Necalli hoisting Chun-Li by her pretty hair up to the sky in primal dominance, Relius using Ignis to pick up Mai by her face and holding her body up for display before he 'experiments' on her... Mature and Vice laughing at Athena for embarrassing herself in front of her fans... So on and so forth...
That's the side that tends to happen to me, at least, when I play, though that doesn't mean the other side isn't without its merit either. Like [Tekken] my Lili coming across a Lucky Chloe that clearly doesn't know how to fight as well as she can... On normal circumstances, it would be easy for me to just beat her and move on, but I was never into running over those that don't know how to play as well as I do. It's no fun to me to win so easily. so, perhaps after a couple of rounds Lili wins easily, and, out of the sake to prevent boredom, she feels she can win no matter what Chloe does. After all, she's barely been able to touch her. So, Lili feels she doens't need to dodge Chloe's kicks anymore. Even if some connect, she'd probably not feel much pain... Oh,and on top of that Lili stops using her useful combination attacks and just uses single blows... No need to use the powerful stuff in a low-quality battle like this, right...? "Just the basics will be more than enough to deal with you..." she thinks...
But, something happens because of this; it exposes the fact that the dominating Lili actually has poor blocking skills of her own, and Chloe has many confusing and surprisingly strong kicking attacks in her arsenal... She just needed the opening Lili willingly gave her to use them... Things even out... and suddenly, Lili begins staggering back... Attacks slam her beautiful legs knocking her off balance... She tried to get distance only for Chloe's leaping somersault kicks to catch her off guard... Chloe begins evading Lili's retaliation blows and using her own legs to throw her about the place... The tables turn and suddenly Lili is the one losing, and panicking. She indeed was the stronger fighter here, but she let her arrogance get the better of her, and try as she might, she let Chloe have too much liberty with her... Before she knows it, a powerful smack of the hand clocks Lili on the side of the head and floors her, and that familiar sexy moan of hers echoes throughout the fight arena... and the last thing she can hear before she passes out, her body crumpled up on the ground...
"Guess what...? You just lost to Lucky Chloe...!"
Utter humiliation... and it was all self inflicted on my Lili. Chole nurses her own injuries, but ultimately dances away in happiness knowing somehow she managed to beat that other blonde girl that was originally dominating her some minutes prior...
....oh, dear. I seem to have written way more than I was expecting to... Bad habit of mine, lol. Tends to happen with me considering I write fanfiction and have a vivid imagination while playing games, but yeah, tldr, I tend to lose to stronger opponents more often... but I think I like the embarrassment of losing to a weaker opponent better. Both options are quite good, you know?