I use paratroopers a lot and they can be fiddly. Sometimes they refuse to go and after a lot of reading and testing, I still cannot figure out why.
However, this has become a lot more rare for me and when it does happen I can always 'unjam' them by deleting the transports and re-deploying them. This of course assumes you've done everything else right (not flying through any contested airzones, set the order correctly, drop is within range etc...).
What I find a lot more reliable than how you've done it is to setting the order for one division at a time. Complete that drop. Delete that order. Then repeat.
I never set all the orders like you have anymore.
Similar to what others have suggested, when in doubt, save and test doing shorter drops from other air bases after having deleted and re-deployed your transports... if that works, then repeat for your desired drop. This is fiddly but you're presumably not going to be doing paradrop all the time so personally I never find it a problem. Also paradrops usually only occur when something big is happening, so I don't mind pausing and slowing things right down at that point.
A final note... I can see in your screens that while you have air superiority, their are enemy fighters active in the region. I've never figured out the exact pre-conditions, but even when you have air superiority, if their are enemy fighters in the airzone there's a chance you'll take massive losses on a paradrop, as much as half your division (per unit) or more. I've seen this even when doing paradrops in China ... I had Bf 109s, they had biplanes, and I had massive airsuperiority, but I still had ~50% casulties on my drops. If you drop on region with static AA you'll take similar losses.
From your screens it's also clear that you're dropping in different zones and having to fly across several different zones to do it. If you're getting 1-2 successful drops, in addition to what others have said, it's possible the airsuperiority changed in one or more of the regions you're flying through. And/or... It's also possible that the game dropped the first 1-2 that were 'OK' and then got stuck when it came to one that was not 'OK' for some reason. Dropping one at a time makes it much easier to isolate issues (and things you might have missed) like this.