Easiest thing, get yourself a quality new tire.
You're wasting hours of your productivity time trying to figure out what's wrong.
Also, make sure you're not pinching the tube or any parts of the tube is sticking out and not sealing properly when you're pumping it.
I inflate the tube by a little bit before I start inserting it in the tire, most of the time I have to double check the tube by where the valve sits. I find it thats where most of my tube sticks out.
Good luck!
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