At about the middle stage of treating my phimosis and now I have some questions

So I'm a 31 year old with phimosis, I've had it all my life. Researched it a ton (that's how I ran across this forum).

I used to be unable to even see the entire urethra while flaccid lol.

I actually thought I had scarring or something because it was so sensative so I never attempted to retract because I thought I might tear something.

I had a girlfriend for 6 years and we had a good sex life with my phimosis however there were plenty of times when I'd get hurt because it'd get stretched too much and of course she'd have to be wet enough... things like longer "strokes" were not possible because it would get pulled and hurt. I couldn't really just shove it in, she had to maneuver a certain way sometimes especially in something like missionary. So it was good but could have been better without the occasional frustrations or inserting penis rituals.

Anyway we had sex without condoms, although I found condoms to be easier to "go harder" if you will... but obviously it didn't feel as good... the tradeoff is I got hurt less.

Since I became single again I decided I wanted to do something about my phimosis because it was a source of feeling like something was wrong with me.

I bought the novoglan and it did help enough to get to where I can get my foreskin behind my head while flaccid.

Of course I do this stretching routine in a hot tub because without that water there is no way my foreskin is even going past half of my head if dry. The foreskin definitely needs to warm up first.

My foreskin behind the head was of course was my first encounter with smegma and it's way too sensative to even touch the head at this point, so cleaning (with only water) isn't even happening right now.

Before I attempted to put the ring behind my head I'd put the ring over the largest part of my head and get a slight errection to stretch the ring out more then I would flaccid. I did this for a while because I didn't want to get paraphimosis.. that's like my biggest fear lol.

I did put the ring behind my head before but I was frightened to get remotely errect so it was really just to say wow I can get the ring behind the head now.

But today was the first day that I attempted to put the ring behind my head and get a slight errection. There was a bit of a stretching sensation which was kinda nerve racking lol. But overall it was not a big deal to lose the errection and the head didn't feel like it was trapped with blood at all.

So right now I am kind of at a transitional point where I can get a semi errection retracted and the band is definitely tighter then the shaft is wide so I assume masturbating while trying to get the ring stretched by the shaft is the best method for now?

I have a couple questions.
1) Sex - when someone gets rid of phimosis as I hope I can. Do you just put the penis in with the foreskin forward or do you retract it?
2) Does the head desensitize enough to the point where you can actually touch it without feeling like someone is going to kill you? A drop of water actually hurts a bit right now. Will doing something like letting the air hit the head for a couple minutes a day help? Because right now everything is in the tub for me. The reason I ask is because I want to get the smegma off one day, it looks gross.
3) Oral sex - I like it and I would like to receive it in the future... Should I expect that one day I'll be able to retract it dry and receive a bj where the woman won't be eating a bunch of smegma?
4) Lubricants... would you suggest using them in the beginning stages of this.. it just seems so counter intuitive because you'd figure once you could retract without pain that the vagina would be wet enough but then again I am not completely sure what it's like once it's in. I just don't want to get hurt or tear.. that's my new fear now that paraphimosis is not a big concern.
5) I read that allowing your head to be exposed while in your pants was a good way to toughen it up a bit. Right now the thought makes me cringe because like I said a drop of water hurts and even a moist tip of the finger hurts let alone cloth with movement.. but is that smart? It seems like it might not be... for instance right now when I let the head get dry and foreskin get dry it seems like it's not happy. And plus the inside of the foreskin is a mucous membrane so having it dry out seems pretty stupid... like flipping your eyelid inside out or pinning your lip so it remains exposed to the environment. Thoughts?