Just checked the fuel pressure specs. for the 300 I-6.
1987-1994 should be 45-60 PSI
1995-1996 should be 30-45 PSI.
Makes me believe 1987-1994 have three pumps and was changed to two in 1995.
If gas squirts out the FPR's vacuum nipple, the regulator is bad. No gas present, leave it alone, it's fine. The regulator keeps the pressure from going too high which is why pressure should go up when the vacuum line is pulled off.
I just checked the part #'s, the L6 got a different regulator (56psi) CM4763 than the V8's CM4764 (45psi) and that's 1987-1995 apparently. The vast majority of my experience is with the V8's.
And yes, on a failed regulator, as I said, if the diaphragm is leaking, it will both bleed down the rail and result in fuel in the intake because the engine will suck it in through the vacuum line straight off the back of the regulator. This is not an uncommon failure and easy enough to check for by pulling the vacuum line and checking for fuel.
The vacuum nipple on the regulator diaphragm is a somewhat elegant way of reducing fuel volume outside of the pulse width of the injectors. In low load situations when less fuel is needed, the ECM is calibrated to expect less fuel than would be commanded via pulsewidth which is likely due to the pintle-style injectors being unable to cleanly meter fuel at those short pulse durations. As you increase load, and subsequently decrease manifold vacuum, pressure will increase toward regulated. At WOT, you should see full regulator pressure at the rail, which is the same pressure you should see with the vacuum line removed.
The old 5psi Vortech supercharger kits as well as the nitrous dry kits for the 302 had a valve assembly that tapped into the regulator vacuum line. When under boost, the Vortech kit would divert some of that boost to the regulator, spiking pressure beyond stock. The nitrous kits worked the same way, using regulated bottle pressure to work the diaphragm in the regulator the other way, increasing fuel pressure and enrichment. Was a pretty smart way of doing it with minimal complexity, but of course you are still limited to the flow rate of the injectors at that pressure, so there were limits to both those kits.
Before the Tw33ker and other EEC-IV tuning devices, a "calibrated MAF" like a Pro-M or C&L would be used (I've owned both) and/or a Holley (or other brand) adjustable FPR to dial in your A/F on the dyno if you increased injector size to accommodate other upgrades you'd made. The adjustable FPR's were particularly helpful for the SD cars, less relevant if you had a MAF car (stock or converted) with an aftermarket MAF that was "calibrated" for your injector size. Later on the LMAF became very much "standard" with an SCT chip and dyno tune, which allowed for very large injectors to run perfectly.