New timing chain, can't get distributor to line up

Yeah you are overthinking it, but before you put the cover on, you might want to actually put the chain on first , lol.

Seriously, the included pic shows your intermediate shaft is over-rotated is all, as is your Vcan
If the rocker gear is installed, do NOT rotate the cam more than a few degrees and if you encounter resistance STOP! and back up.
Rotate the I-shaft about a third of a turn clockwise, being sure to re-engage the pump, so the shaft drops all the way down again; then re-orient the cam sprocket back to where you have it in the pic. This should get your Rotor close to pointing to the frontmost driverside intake bolt; don't fret if the I-shaft slot is pointing somewhere else cuz it is the rotor's final resting place that counts.
From here Rusty and others have you covered in post #5 with the 180* deal.
The only reason I used the 1/3 of a turn, instead of slot orientation, is because some aftermarket D's have the distributor drive indexed to some other place than Mopar does, and so the slot to #1 doesn't work on those, whereas the rotor to #1 does.