I believe you should use the same parameters other than size when determining upsized or not. That is if you have parallel sets in one conduit, then you compare to the smallest Code-compliant size of parallel sets in one conduit.A situation I've wondered about is, when increasing size to curtail voltage drop will prompt a change in the number of parallel sets. ...
Now someone may bring up that the smallest permitted parallel conductors are 1/0... and technically they just answered their own question. Consider it a loophole in current wording.