I don't harden up or cut water lol. I am a powerlifter, I stay nice and bloated all the time.
I am not even going to lie and say I know anywhere near as much about bodybuilding training as many guys on here.
All that being said, while winny increases collagen synthesis and makes larger tendons it also makes them weaker. It has to do with cross linking integrity. Even though winstrol makes your tendons bigger there is less cross linking so they become weaker, and more likely to tear, so for that reason I may suggest going into a lighter rep range.
Conversely, I know a powerlifter who uses winny every cycle, and loves it. He has had no real injuries aside from the normal small tweaks. He also uses EQ and Deca a lot though, which help strengthen tendons, so that may be why he hasn't had the joint effects from winstrol.
As far as from a cutting perspective, I don't know how much it would affect you. I know a lot of guys who keep their liftng the same and only alter diet and cardio to cut. I know others who change it all. I don't cut so I can't really offer an opinion.