Those are happy roots in a perfect situation. Fron the dry desert of New Mexico, USA, Kudu to Cuba! You can literally grow nearly any orchid there! Your Sherry Baby may become a plant bully, she looks so happy!
If your primary concern is losing the flowers then don't repot. If it's the long term health of the plant you care about then repot. It's better to know the state of the root system now when you can still correct any issues. If you lose the flowers guess what? It will bloom again if properly cared for.
If you follow Philip's advice you can't really go wrong.