One of the things that I'm going to do in my game, is to make entire categories of items unusable or gimped across entire bands of space. So as you progress (the leaderboards are mainly based on how far in "the direction of difficulty" you can get) you will eventually get to a point where you have to abandon your favorite strategy and come up with a new one.

Even without this, due to the rarity of items that have little penalty for benefit, you will often have to improvise, as your required item will likely not be available with exactly the right combination of compatibility and stats.