So, absolutely no drag on the way home. Then, I talked to Northracecars.com about it, and he suspected the prop rod needed more adjustment, but after listening more thought maybe booster issue or MC sticking. lol... I get it... it's very confusing, especially with the intermittent-ness.
Clues:
1. Typically drags somewhere between 5-15 min into a drive and clears up on the highway
2. Can be reset or cleared up with a heavy linelock brake release
3. Does not happen when booster is disconnected
New clue:
Turned the booster rod in a lot (maybe another turn) & reconnected vacuum. Didn't make it half a block before noticing drag. Pulled MC out from booster to turn the rod all the way in, i.e. no adjustment is left, and noticed this grease squeezing past the inner part of the rod. hmmm
On the next test drive, I noticed absolutely no difference in where the pedal engages. How is that mechanically possible? If there's more of a gap between booster rod and MC plunger, there has to be more pedal before engagement, but there simply is not. But... I couldn't say for sure if there was any drag.
I'm getting

ititis, at this point. I have a spare 93 Cobra booster on the shelf. If I also have another 93 Cobra MC, I'm gonna replace both this weekend, and if not then I'll order and replace both soon.
Black Jack has consistently been a car that likes to come up with some tricky ones for me (compound drivetrain vibration I had to go through absolutely everything to fix, intermittent spark issues that turned out to be a dying MSD box I couldn't easily bypass, thanks to the then-recent wire tuck, to name the two big things). It is just the fox I needed to challenge myself and learn new things, I guess. At least it has been reliable and held together with an old high mileage powertrain on a 150-shot to this point. *Knocks on wood*