Questions are never a problem! Ask away. I hope this answers your question:

I've never had any problems getting roots out of the clay pots when transplanting. if it doesn't pull right out, just soak in lukewarm water for a good half hour + before you try and pull the orchid out for transplanting.

I've had issues with plastic, and ended up having to cut up a few plastic pots to get them off the roots. Never had to do that yet with clay, but with clay you can always wrap it in a towel and tap it with a hammer to break the pot. Easier and less traumatic on the roots than cutting into them like I've had to do with a few plastic Cymbid pots.