I've had flats that made my toes bleed (pointy shoes of course lol), many times. For some reason my pointy kitten heels though seem to do just fine... However higher than kitten heel and it puts a big strain on my foot muscles and balls of my feet. I honestly don't even know why I keep going out clubbing in heels when it sometimes just completely destroys the night. I have learnt though that if my feet are already hurting before I've even left the house to go clubbing, the I need to change shoes.
It depends on the brand & quality obviously, if I wear my Jimmy Choos I can walk in them for ages but then my feet are rather narrow so that's a benefit. Louboutins are also better than cheaper options but then I use inlays with those. If you wanna go for a more casual heel I'd stick with Vagabond, those are seriously super comfy and very affordable!
heels yes. platforms no. its not the height its the discrepancy between platform a heel. if the platform is equal or nearly equal to the heel then im good. but i not wear heels bc i always run around and i end up getting blisters. or breaking my shoes.
heels are murder, it gave my mom bunions so i'm not about to repeat my mom's mistake but if i absolutely had to (like for a friends/relatives wedding) i'd wear it but no more than 3-4", then i'd gladly bury it in the back of the car afterwards
Heel's aren't painful on my feet as they are on my knees. One of my knees is bad so I can't wear 3" and above for more than a few hours. Less than 3" I can walk all day. But as I'm getting older I find that I prefer cute but comfortable flats or a low wedge heel.