I'm currently in 1st in a 10 team H2H points league with 10 extra bench spots and 3 IR spots. Looking ahead to the playoffs I have a plethora of guys who will/might sit b2bs during the playoffs including PG, Kawhi, Porzingis, Richardson, Conley, and Oladipo (and Bagley, Otto Porter Jr, and Kyrie if they play again). Would it be smart to look to sell some of my players who will most likely sit games even if I lose a little value in the process?
Yes, but ONLY because you have so many. If it was just 1 or 2, I'd stay put.
Any one or two of them you would be more inclined to sell compared to the others?
Selling one of PG and/or Kawhi seems like a good place to start. Maybe package one of them with another guy on your list for a top 10-20 guy.