Please help!! no oil pressure after oil change!!

I'm thinking bypass has to get high enough pressure to make that spring compress far enough to open. Even if it did he should have some pressure cold I would think. Not sure he had any at start up with a dry filter. To me, nothing was being picked up at all.
The chunks from the strainer look to me like old hardened cork gasket and possibly timing gear chips.
I would take another look at that intermediate shaft and try to assure myself the shaft is not slipping. Also it's possible the gerotor shaft could have spun if something bound up the pump.
I would not install a "dry" filter.