You are talking automatic upshifts, so; IMO
I would drop the VB and airtest the second gear servo and the high drum. If they test Ok, then into the VB I would go. I think you need more spring on the second gear shift valve, to fight the higher line pressure. This will keep in second longer and simultaneously delay third.
Adjusting the KD will never correct a basic mis-matched shift sync.
IMO, and on the street,
if the shift-sync is gonna be mismatched,I'd rather have the 1-2 shift a lil earlier compared to the 2-3...... cuz it's just more comfortable for me around town.. If I need it to stay in first a lil longer, well, that's what the shifter is for.
What this means is if you can't find a stiffer spring for the 2-3 shift valve, then put a softer one in the 1-2....... and readjust the KD to bring them where you want them. If this makes the shift too crisp, then back off the line pressure a tad and work the KD again.
BE prepared to do this several times until you get it right for you.
To make it easier I drilled and tapped the case in line with the line-pressure adjuster, for a pipe plug. Line-pressure adjustments are now easy and fast.
While the VB is off, check the Second gear band apply lever for ratio. It should be in the 4s for performance, else you will slip the band and wreck your drum again