So after thinking about this for a few days, here's my plan of attack...
Thursday, get the car home from the airport, one way or another.
Friday, order new fuel pump, and place order with Pherable.
Saturday, ship ECU off (may be able to do Friday, not sure yet).
Weather looks iffy over the weekend, so will be a good time to get the garage straightened back up (still a wreck from the last few months of car work).
Monday -> Friday of next week - remove passenger knuckle and deal with wheel bearing, and remove and replace transmission. Also plan on sneaking an oil change in here somewhere. I've gone roughly 400 miles since I threw it together. The block and head neither were "brand new machined", so wasn't as worried about a strict break in procedure. However, given the head gasket problem, leaks, and such, figure now is as good a time as any to reset the slate.
Transmission swap is 95+% likely at this point, I just don't have a good feeling about the one in there. Shifting felt a whole lot more "notchy" than what I was used to, and I know the old one never had a lick of issues, and I know its history. The original OEM clutch made it over 200k miles with the original owner, so the original transmission should be more than fine. The poor car probably only hit VTEC a handful of times before I took ownership. Also going to inspect the clutch while I'm there, it should be fine, just want to take a peek.
Timing wise, that timeline should have me buttoned back up by the time I get my ECU back, so hopefully I can get it on the ground, plugged in, and get ready to beat the absolute hell out of it. I'm just past the point of being done with dealing with "major things" on this car for a while.