Yes, it will. I used to have the same setup. IMHO TacStar is just shy of worthless. I would recommend the Mesa Tactical aluminum carrier... more expensive, but you get what you pay for.
It'll work fine. I have one and no problem. Just make sure the sidesaddle is for the Mossberg 500. They make em for other shotguns like the Remington 870 too and that wouldn't work.
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