I use my selfmade silicone sleeve as per: dickerschwanz - Silicone Sleeves - Make your own
Its rather easy to roll down. I had 2 versions. One thick and one thin. The thick one rather hard to roll down and as you say too rigid.
The thin one allowed some air to go under the sleeve. I adjusted it with some other sleeve over it and it worked very fine. Could feel pressure more inside.
Too bad the silicone is so expensive or I would produce much more as I have some more ideas.
Yes I have followed your homemade silicone exploits and when time permits I will see if I can make some too. Making thin wall sleeves as you have done should help but I have compared the ABSilicone sleeve to others of similar thickness and they do feel softer hence my conclusion that they must be made of a very soft silicone compound. Not sure how you would go about getting the right mix to replicate that.