@Stefanhope, you definitely shouldn't be able to fit the bullet back in there by hand. Think about it... If you can slide it in by hand, what's to stop it from wiggling back out?
Do you have a set of calipers? Measure the outisde diameter of the bullet, should be 0.284". Measure the inside diameter of the neck, should be about 0.280". You'll need the force of the press to push the bullet down into that - but it means the neck will grip the bullet like an elastic band as it's forced open.
Lube on the inside of the neck helps the expander ball (the bulge on the spindle in the middle of your resizing die) force its way through the neck. But you don't want that lube - waxes, oils, etc. - contaminating the powder you're going to put in there later, so remove it after you've resized. Use alcohol, soapy water, Q-tips, whatever.
YouTube. Reloading manuals. There's lots of resources out there.
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