Bogged down While In Gear And Sputtered During Acceleration

anddddd maybe I spoke too soon. It is now back to falling on it's face when put in gear. I have not installed the new lokar kickdown cable so have not been able to go on a real drive yet. Initially after putting the new holley on it went around the col de sac without shuddering and everything seemed fine but after I tried to dial down the massive cold start idle (2300 rpms) it now is acting the same as before the new carb

The timing was wayyy advanced and after dialing it back down to 14ish it idles ok but shudders. Vacuum at idle is 17 and the gauge needle has a slight bounce (about .25). When put into drive or reverse the vacuum falls to 7ish.

I am really thinking timing chain skipped now. I have triple checked the gaps, plugs, wires, voltage, fuel pressure, tested for vac leaks, rotor...........I even checked the play of the chain by watching the rotor as I moved the crank bath and forth.
This is driving me crazy.

If the chain did skip, would the timing get retarded?