In a perfect world, theoretically the system should hold pressure indefinitely, (this isn't a perfect world, it’s a GM

). It doesn't matter how long the system holds pressure, just so it doesn't drop below 55psi after 5 minutes. At the next start up, the pump will prime the system and satisfy the fuel pressure regulator. It's not a bad idea to allow the pump to prime and shut off before attempting to start the engine each time.
The size of the leak determines how long the system will hold pressure. If there's a leak anywhere in the pressurized portion of the fuel system, the fuel pressure gauge will indicate a drop in pressure. If the fuel return line leaks, the fuel pressure gauge will not indicate it because the line is not under pressure.