Just a thought... Before I plugged my distributor in, I tried to start it. It turned over without a problem. Maybe I plugged something in the wrong slot?

 

But you did get it running again, right? If you had plugged the distributor in wrong, the engine wouldn't start. Is the starter still grinding? You'll want to check the gear mesh and shim the starter where needed.
As far as the engine turning over better with the distributor unplugged, your timing might be swung out of whack. Timing too far advanced will try to push the pistons back down too soon, making the engine harder to turn over.

 

Sorry, that was more of a mental note for what I was going to try when I got home. Before I plugged the dizzy in, the starter would turn the engine just fine. Yes, it did not start, but there was no grinding. I'm wondering if my timing is so far out of whack that it is making my starter slip/grind. I'm waiting for my wife to pick me up from work. Ill run home, unplug the dizzy and see if the starter will turn the engine. If it does, I know its the timing.

 

the timing would not affect the starter or the mesh between the flywheel. could just be a coincidence that the bendix gear is going bad.

 

The timing can indeed affect the starter. Not the mesh directly, but if the timing is off enough to cause a backfire it can kick back and damage the bendix gear, which would then lead to engagement problems.

 

I pulled the power dim the coil and it is indeed the timing. Also, my valve covers are leaking due to a missing bolt. Thanks everyone!

 

I turned the dizzy and it started without grinding. I went to take off and it died. I'm assuming its either the timing still being out of whack or the carb needs to be tuned even better. I restarted it and gave it a ton of gas and the engine felt like it was fighting me. Heard what sounded like metal hitting metal so I parked it.

 

What I was getting at is if the timing is so far advanced, the plugs are going to fire way before the piston gets to TDC, which is going to want to push the piston back down too soon. That will make the engine hard to crank over, put more strain on the starter, and the engine might even literally stop rhythmically at every revolution. No, it won't affect gear mesh, wasn't suggesting that.

 

Try about 12* BTDC. And see if the starter kickback is still there. Then set the idle and take it for a spin.

 

That metallic sound may also be extreme timing error. If it's too far off it will knock like there's an engine problem. Get a timing light on the engine once you start it, and make sure it's set correctly.