Not trying to be a smart ass but are you sure you’re pulling the #1 plug and not the #5 plug?
Are you rotating the engine by hand or using the starter?
The reason I’m asking is because if you’re using the starter to rotate the motor by the time you hear the compression it’s usually gone past the zero timing mark.
Remove the #1 plug, then with a breaker bar and a short extension and the correct socket rotate the engine until you feel the air escape through the #1 plug hole, if you don’t feel any air escaping but you see the pointer on the 0 timing mark that means your on the exhaust stroke not the compression stroke, just keep rotation the engine until you feel all the air escape. I’ll even stick a long pencil in the #1 plug hole and watch it as it comes to the very top and if I see if start to go back down II know I’ve gone to far.
At this point try dropping the distributor in, remember the teeth on the cam and distributor are angled so the distributor will need to be rotated to compensate.
When the distributor drops in you could be ahead or behind the #1 plug wire on the distributor cap just pick it up and re stab it so that you will line up with the #1 plug.
One last thing….. if the distributor points to the #1 plug but the distributor won’t full seat more than likely your not lined up on the oil pump shaft. Hold the distributor and slightly rotate the motor again and the oil pump shaft will rotate enough to let the distributor fully seat.
To double check everything (if you use a pencil remove it) and rotate the engine again until you feel the compression start to exit the #1 plug hole and watch to see where your timing mark is and the check the to make sure you’re on the #1 plug wire.
Reinstall the #1 plug put the distributor cap on, snug but do not tighten the distributor bolt, set up your timing light, remove the spout connector , start the engine and set the correct timing by moving the distributor or what ever timing you chose, then tighten the bolt on the distributor and plug in the Spout connector.
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I hope this helps and makes some since?