There's lots of good advice offered so far.
My only other thoughts are...
* Your 'muscle memory' is tuned to the plastic razors. You may not be actually slicing through the hair, but scraping instead. Your photos show stubble under your chin area. Ride the cap of your DE and do a few strokes. Lower the handle a wee bit and stroke some more. Keep lowering the handle until you feel (or hear) the blade start to cut. Don't over do it and ride the safety bar too much as then you are into 'scraping' territory.
* Tried any other decent soap? Stirling would be good, or Haslinger for a start.
I too used TOBS for some time but then one day I read the list of ingredients. Things like tetrasodium edta are not really good for you.
I'd try another good soap if you haven't already.
I also used Proraso Red, Green, Blue, and White (Sensitive).
Here's what the Sensitive has in it.
https://incidecoder.com/products/proraso-shaving-soap-in-a-bowl-sensitive-skin
If it were me, and having skin problems I'd be ditching that Proraso.
Funnily enough I ditched all the Proraso products once I got into more aggressive razors (Timeless .95, Karve with #F, and #G plates).
Those soaps worked for my milder razors, but not so good with my later razors that shave closer (plus I didn't like the Proraso or TOBS ingredient list).