Good evening. For starters i'm assuming that pot is plastic due to cracks and not chips. Strongly suggest growing in cheap black plastic nursery pots for this reason among others.
Plant is far from root bound as pictured. unless underwatered of starved for food. When a pot that size is dry every other day it approaching rootbound.
When it comes time to move. Let the medium get a bit drier than normal. Gently squeeze the pot between your thighs while sitting. And rotating the pot until you realize it is free. Lift the pot from under neath with your good hand. Place the stem between the 2nd and 3rd fingers of your off hand. Invert. Voila. Plant, undamaged in hand. Light spritz of water to the roots if a minute or longer before transplanting. Easy.