I personally would not pull out my chickens feathers. Around this time of year chickens go through a molt and I go around there pen and collect the feathers they have shed that have landed on the ground. I then bring them in the house and soak them into a bucket of water with dish soap added in. I let it soak for a while and then rinse each feather one by one in some running water and place them flat on a paper towel to dry. Then I place them into a plastic zip-lock bag and put them into the freezer for a week or so to kill any parasites that could be living in the feathers.
Feathers do hurt when pulled outside of moult. Many feathers for sale for crafts in big bunches are from chickens killed for the purpose. Small time collectors and craters often just pick up moulted feathers.
Yeah, it hurts. You only pull two feathers for DNA sexing for this reason. At the aviary, we constantly had to keep people away from our peacocks because they would try to pull out tail feathers. Rehabs will often have to keep gunked up birds that have bird glue or some other hard to break down substance in their feathers until a full moult. Pulling out all the feathers isn't an option. You can see this in self-plucking parrots. One medication out there is an endorphin blocker. When parrots pluck their feathers, there is a jolt of pain. However, this causes the body to reduce endorphins, so a feeling of pleasure can follow (similar to humans who cut). By blocking the endorphins, the bird only feels pain, and is more likely to stop the plucking behavior. So yep, there is pain, and in the case of new feathers, blood.
A natural moult can put a lot of stress on the bird, usually with them needing more nutrients during this time of feather replacement, and some will stop laying during a moult due to this. A large plucking sounds painful and unsafe for the bird.
I would just put a moulting bird into a pen, and collect the resulting feathers.