Chevrolet started running 3 line bypass pumps with a return to the tank on nothing crazy,stone stock, carbureated small blocks in 1979. There is no reason that good bypass regulator would be any more liable to fail than the regulator you put on there.
@Bextreme04 gave you good advice and good reason why you should run a bypass. There is one more reason and maybe even one of the problems you are having. With a 2 line pump,fuel pressure is held against the needle and seat when you park. As the fuel heats in the line in a hot soak,it explains the extra pressure blows the needle and seat open,extra fuel spills into the bowl and floods the manifold. On a hot restart you have too much fuel,not enough air you pump the pedal and it starts,because of the extra air,and the black poof out the tail pipe is too rich mixture. With a bypass the extra fuel bleeds back to the tank