Actually that was filmed in my garage. That brand new PCV didn't seal in any position. Neither did the one before it. Replaced with an RJC check valve style.
Mine has dropped below freezing a few times. Wouldn't start the bike, even after attempting to warm with lights on. Haven't experienced it often enough to resolve. I don't ride in freezing weather that often any longer.
Are you sure the cylinder is pressurized? Do you hear air escaping when the valve opens?
Make sure you rotate the piston to TDC before you remove the springs.
If the timing set fails, the pistons & valves may meet.
There is a good amount of disassembly required to change the timing set. It often snowballs into a much larger project than initially thought. Oil pan is usually dropped & cleaned. Oil pick-up inspected & cleaned. Might as well change...