Good question.
My experience is that, in general, getting better quality components (including conditioning) is preferable to more. But it is highly dependent on your situation. If it were me… using a power conditioner… I would not use two, I would upgrade the one. It is more a part of my design Philosophy than anything. Stringing things together the number of permutations goes through the roof quickly (add sequence dependent). Also, more connections… and difficulty in assessing the difference between a 2x more costly power conditioner (for instance) and stringing three things… just because stringing improves the sound doesn’t mean that the 2x component would not have been even better.
For instance, I have a great streamer and a Ethernet regenerator did not sound better… but added connections and powered equipment in a small space. So I got rid of it.
So, probably a generalization would be difficult. I try and keep things simple.