I found a continuity problem. It's still possible to have Chloe assigned to clean the bathroom wearing Amy's maid uniform before you even unlock or order it. The dialogue specifies that it's Amy's uniform as well.
Personally, I found that the uniform was a bit too much of a challenge to unlock. As it was I had her at level 4 and maxed stats before her obedience would go high enough to unlock it. This also meant that I had options for level 2 and 3 punishments that were empty. Based on the tracker and punishment levels she's clearly intended to get it before she levels up. It seems like lowering the requirement and locked her leveling up would help quite a bit.
It's just my feeling, but it also seems like she leveled up really quickly. It was more effort to raise her other stats, but she shot through the levels. Linking obedience and attitude to the quality of work also meant that it was relatively random. I had to wait until she did a good job before I could reward her, but as soon as she got two good jobs in a row it would tend to shoot up rapidly because now you're reinforcing two stats that result in her doing a good job every time. There's no longer any justified reason to punish her.
So the effect is that it feels like a big grind just to get her obedience up, then you're left with most of the content intended for her training effectively in the past and no longer necessary. This is a fun idea, but it really needs a lot more tweaking.