After examining all options we decided to modify the pillar in the area shown. A gradual taper was needed starting at the mid point of the pillar working down to a 3/8" gap at the bottom.
The drip rail was removed then the pillar was cut using a thin cutting wheel. The pillar was bent into its new position then prepared for welding.
The tack welds were ground smooth then JB Weld was applied to fill in any nooks and crannies.
And we have a respectable "3 tongue depressor" gap on the inside. This will be perfect for that piece of molding.