Pulled back — living with a bare head

At first I always covered up my glans. I mean, washed it then covered. Dried it with my tow and then covered again.
After a while I've forgot it to cover. Did not really think about it.
If I'm not actively retracting, i pull back during shower and leave it, when it slips forward it slips forward.

2.5 and 2, aiming for 3 and 3

I didn’t uderstood what you meant by saying that your penis is pointing down now.
Why it used to be up and not in your underware when soft before pulling back?

All the way down, completely flat on the shaft

For a short time the skin will remain bunched up a little bit away from the glans, but it will soon be bunched up behind the glans.

As for the other questions: are the video and the photo your penis?  Because then I can say it looks like there's no tightness whatsoever since that foreskin goes back very far on the shaft.  If it's not yours, well, it's not necessary for it to be able to do that, so don't worry!

Not my photo/video. By the responses in this thread, it sounds like most are able to pull their foreskin all the way down the shaft, smoothing out the inner foreskin (just like in the video). I have no problems pulling my foreskin all the way down the shaft when completely soft. When hard I'm definitelynot able to do that, the farthest I can pull back is right behind the head. If I tug really tight, I can expose a bit of inner foreskin, maybe about 5mm/0.5cm - not even half the width of a pinky finger. As soon as I let go, most time it will stay behind the head but not always.

Like you said, it's not necessary, but I would like to be able to have my foreskin move more freely. I've flirted with the idea of having my frenulum cut, but don't trust myself enough to do it on my own. My only worry with a cut frenulum is that the foreskin would never stay behind my glans when erect because nothing would be there to 'stop' it from rolling forward.. I should probably see a urologist, lol.

Ideally, all the way. But do not despair when you can't.

A penis has a life cycle. When kid, only meant for peeing. Every bit set to keep the tickling parts covered for later. When adolescent, meant to orgasm, as much as you can. Half open, or anything in between will do fine there. After that, meant to enjoy. Only then better without any speed bumps. A smooth stroke back from top to root. After x-thousand awfully short orgasms you finally learn to keep the best for last. In general that is.

Then all penises are different. But all are worth to have it. Some slide back all the way from the start. Others keep wanting to return to boy-mode no matter how often you train it spooning or any other trick in the book here. So in a way, that is normal too. If you could study porn on the web in stead of getting turned on by it, you see it. All different. Yet a smooth slide down, and even up, that is the goal. No speed bumps. The difference with training is you get there faster. While other guys have it by nature and might not even understand what you are concerned about.