I too have a '95 softail with a starter button problem , that has been driven me crazy. If bikes sits for a couple days, it takes several stabs at the button before it will engage starter, and then it might disengage requiring several more attempts...once bike is warmed it starts real easy...hit button and it fires right off. ...one thing i have found that helps when bike has been sitting, is to turn on ignition switch...push bike out of garage...leave it sit for several minutes with switch on,,headlights and all...it will fire right up....i guess i need to break down and buy a new switch.
At first i was thinking i had a starter issue...but after carefully watching how it starts..ie hot/cold...i have come to belive the problem is with the handle bar switch
As for oil pressure..when bike is red hot and sitting at a trafic light...it runs down to about 5 lbs,,,20-25 under throttle...motor has 47000 miles on it...mild cam, Jims roller lifters , SE ignition and a S&S carb...never an oil leak or base gaskets, the motor is quiet and tight

....i have run this bike hard...it is set up with apes and jockey shift with suicide clutch...upswept fishtail exhaust, and an old style round oil bag...50's style flames