You need new gear and roller assembly.
Or a new head
 
You need new gear and roller assembly.
Or a new head

Alright I thought it might be roller assembly. I probably stripped it or just normal wear and tear stripped it. I bought a new one so will give it a shot when it comes.
 
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Just an update for those with future issue. I replaced the roller assembly today. Before replacing the inside of the old one was basically rounded to a perfect circle, but the new one had the D indentation so it would get better grip on the D shaft.

New one worked perfectly like new. Running it now for 30 mins to loosen up the tube some while pumping some chlorine to test it, but all in all was a $30 fix.
 
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