Changing the head gasket will not effect timing. but without pressure on the lifters, and the engine is turned over for some reason like going from TDC to BDC can push oil into the lifters and prevent the valves from closing.
Had a customer a few years ago that was using 30w in the single Command engine, and after running for a few minutes would stop running. Wait a few hours and would start back up. The Command normally calls for a multigrade oil and the straight grade was allowing the lifters to overfill and hold the valves open. I have seen where push rods would get bent from trying to turn the engine over without collapsing the lifters before trying to start.
I normally will remove the lifters and collapse them by wrapping in a clean rag, and inserting a small socket in the open end and putting the whole thing in a vise.
Had a customer a few years ago that was using 30w in the single Command engine, and after running for a few minutes would stop running. Wait a few hours and would start back up. The Command normally calls for a multigrade oil and the straight grade was allowing the lifters to overfill and hold the valves open. I have seen where push rods would get bent from trying to turn the engine over without collapsing the lifters before trying to start.
I normally will remove the lifters and collapse them by wrapping in a clean rag, and inserting a small socket in the open end and putting the whole thing in a vise.