I do it regularly ... but only to check to see if there is a rootball.
Hours after watering I'll place the stem in between my fingers and tip the plant in pot, upside down, I may poke the soil through the bottom holes to get it to dislodge.
While upside down in my hand, I'll check to see if the roots have reached the perimeter of the soil ball or if there is a root ball and I'll then place the pot back over it and turn it the right way up again.
Depending on what I see I'll either leave it in the pot or if there is a good rootball, I'll then up-pot to a larger size.
I won't disturb the soil... as much as I can.
The clear cup within an opaque cup is a good idea.
j