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Are you ADHD by chance?
This was my first thought as well. OP sounds like myself before I was diagnosed with ADHD (type combined) and started learning how to address my symptoms.
As soon as I saw, "... Reading over and over..." In OPs post my mind jumped to ADHD. I, and so many others with ADHD, have to re-read a paragraph, heck sometimes a sentence before our brains wake up and realize that we should store this info in short term memory.
A therapist who specializes in ADHD in adults (it used to be believed that children diagnosed with ADHD would "grow" out of their ADHD as they got older. Thankfully this belief is rapidly changing as our understanding of ADHD gets better). They can help you start to re-work your life to be complimentary to your ADHD instead of feeling like you're trying to cram a square peg in a round hole.
ADHD isnt the root cause for everything, but it definitely influences all aspects of your life in varying degrees.
Information or decision paralysis is also an ADHD trait. Also the inferred inability to self-motivate or get better jobs, and of course like you said, the re-reading with inability to get things to stick.
Yeah, it may not be ADHD, but OP’s symptoms rhyme with it. And they definitely don’t get better with age, you just get better at masking some of them.