1. All controllers are in good (7/10) or even great (8+/10) condition. This means fully functional, no very loose sticks or big scratches.
2. In my experience no. I think the rounded analog is great and highly recommend it, I guess that it makes it a bit more based on your precision with the stick, but not something that makes it harder. The best way I could explain the precision is that the original controller octagon kind of auto-directs your character to an extent, while the rounded is completely based on your accuracy. It can take some getting used to, but Im sure you can understand that.