Spark should be checked at each plug, not the coil.
The vacuum pump, I'm not sure what to do with, but if it's also just a vacuum gauge, hook it up to intake somewhere and read through the link I sent a few posts back. It's got a whole list of tests to perform along with interpretations. Very useful.
Fuel pressure dropping after 15 minutes probably means your fuel pump is dying. The most common symptom is decreased PSI once the pump warms up. It could also be as simple as a bad internal connection in the pump assembly to the top of the tank. I ran into the same issue when doing my V8 swap as the hose would leak once things warmed up a bit. Either way, I can't think of any other reason for your FP to drop. Maybe someone else can.
Disconnecting the O2... I'm surprised it sputtered out. Mine never have. It'll run.. less good, and your fuel economy goes to shit, and it'll run rich to err on the side of caution, but I've never actually had it stall out. Yes, it'll sputter a bit when you first disconnect it while it's working on switching to open-loop mode, but should clean up pretty quick.
As is always my recommendation, fix the stuff you KNOW is wrong first. FP dropping like that is not normal. Also, if you have to prime every time you start up, your FP regulator is toast (has a check valve internally to prevent backflow, so you should never need to prime the pump/rails unless you've had the rails or injectors disconnected and manually relieved FP). A bad check valve points to a bad FP regulator, so that's where I'd start. If you're going to swap out the FP regulator, I'd actually just rip it right out entirely and fabricate a straight connection from your fuel pump to the top of the tank, and install an external regulator/check valve/filter, cause it's a bitch to drop the tank every time you've got fuelling issues. I never did this (until I did the v8 swap and it became necessary) and wish I had, as I had a bad check valve as well, and every time I started the Jeep, I'd have to prime the fuel system 2-3x or just let it crank for 5 or 10 seconds till it started getting fuel. I ended up dropping the tank at least 6 or 7 times before I said **** it, and left it alone till I did the v8.