The funny thing is you're playing the game backwards. If your object in playing this type of game is to beat the game, then I assume you would do so by making the most of what you are given. If I find really good STR armor with +2 Scoundrel for my tank, I am actually happy, because now I am able to use really useful Scoundrel skills without actually putting points into Scoundrel...is your mind blown yet? Sure some items don't make sense, but why do you want to play a game where every single item you loot is an upgrade? If every item you find is an upgrade then you have to switch out armor after every battle, luls.
Also, what if I told you there are ways you could build a party so YOU DONT EVEN NEED EQUIPMENT to beat the game?
I'm just curious: What Scoundrel ability that isn't named Cloak and Dagger would someone using str based armor even be able to use? All of the rest of them require a dagger, which only scales off finesse as far as I know, which someone using str based armor is not very likely to have a lot of.