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I was working on a 28 Tudor yesterday for a gent. He was having the same kind trouble with up shifts and downshifting into 2nd without severely clashing the gears was impossible.

I drove it and was experiencing the same issues until finding the trouble.

Turns out that the cable from the battery to the starter was moved to a battery cut off switch by the steering column.
The relocated battery cable was getting pinched between the cross member and the clutch pedal arm not allowing the pedal full travel. Wasn't much travel lost but it was enough.
The cable was worn to the point it had shorted a few times.
Re-routed a new cable and now it shifts smooth as butter.