I'll ride 58s on my transition set up until they are about 55 and then set them up on a street set up until they are about 50mm, unless they wear unevenly or to different size wheels or flatspots/ chunks.
Same.
That works so well.
Bigger wheels on a "just go fast" board and when they wear down they go on the "curbs and tech" setup.
Obviously you can still skate any wheel on any type of terrain, but some days I just don't feel like doing much, so the bigger wheeled board is best for having fun doing laps round a park.
Also rotating wheels so they wear evenly can double the lifespan of a set of wheels, compared to people skating them down so much that they end up as a 48, 49, 52, 53 mix, going by back toe, back heel, front toe and front heel positions.