Well Doug, at first I would have suspected a worn pump but you have 305 at idle so pump sounds good. Do you notice a sound like the pump is full of marbels when it doesn't drive? That could be the pump drawing air, might explain gauge fluctuating too. Take the rear skidpan down and inspect the pump suction line. Not sure if your trans has a suction line coming off of the front bottom of the trans or not. If it does there is a screen inside the trans to inspect and clean.
If all of that is good and problem presists keep a gauge in the trans pump and come on back with the pump pressure when it will not drive. I might be a clogged orifice to the load piston behind the modulating relief valve. That would keep pump pressure at initial pressure (app 75 PSI) too low to drive.
Later Bob
May have a broken spring behind modulating relief valve.
I think you just have a couple of stopped up trans filters if it's not building pressure for a couple of minutes. Look under the seat for it. Sometimes there's another one under the floor plate to the right of the decel pedal. There's a magnetic screen also to check, I think it's close to the oil cooler.