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FWIW....I have a T-19 behind a 460 and i have the same issue. Clutch is worn but double clutching or giving the throttle a blip will get it to drop into 2nd gear. And the T-18 I had in my F-150 (behind a 400) did it too. My money is on worn synchros in these situations.
I noticed a similar issue with my truck when I first got it.
Previous owner swapped in the NP435, as it was originally a C6 truck. He said the clutch was new (I personally would never use a used clutch). I found that a double clutch down shift and a slight rev helped.
I was still unhappy with how the pedal would return (seemed like it was binding). I adjusted the linkage, and that seemed to cure all of my issues. Positive engagement into second, and the pedal returns nicely.