Do push your self out of comfort zone while stretching or is it maybe more important and effective to do it often and not pushing very hard. Or does it even work without a little uncomfortableness?

I definitely go outside my comfort zone for about 25 seconds per stretch but the other 35 seconds (I do one minute per stretch) I just find a good deep (but still comfortable) stretch

It is best to focus on the actual muscle relaxation than to treat it as a physical test. Do not over stretch as it may cause pulled muscles. Try your best to breathe deeply as you stretch and you’ll notice over time that you are able to stretch deeper.

Yes I would move slowly into the stretch and out of my comfort zone slightly, then hold it for at least 30 seconds or more. And, each time trying to push my limits further.

Stretching should never exceed a pain threshold; instead, go to the edge of what’s comfortable – use props like blocks and straps to support yourself in the stretch – and breathe. 5 deep breaths and see if that unlocks your ability to stretch further to find your edge of discomfort. Otherwise, stay there for another 5, and try again. Do this 3x per session and then move to the next stretch you want to do. Dynamic stretching will also help get more mobility. Dynamic stretching is when you move in and out of the stretch with your breath, kind of like flow (vinyasa) yoga. The dynamic movement can cause you to tear the fascia in the muscle though so, don’t throw yourself in and out of postures… instead move deliberately on a 1 in/1 out count. Good luck!

You don't want a lot of pain when stretching. Some slight discomfort… where you "feel the stretch" is okay sometimes. If you are doing a stretch in the correct position, and are far/ deep enough into the stretch… but still don't feel too much… I think that can be okay too. You are still moving the muscles and maintaining flexibility.
Hope that helps!

I think you have to feel some stretch not pain but definitely outside of the comfort zone. Better to do longer stretches with less push then exhale and push further as it stretches. Anything is better than nothing and if you don’t feel like pushing yourself just do a little bit.

Do it often. Your comfort zone willget wider and wider. Don't overstretch, especially first thing in the morning. Let your body limber up before doing more intense stretching.