Vreg black to battery POS turned out 1.2-1.4 V
This is certainly not good.
The field strength in the alternator is surely lower than it expects to have.
You could try to run a separate wire from battery POS to the White wire. This ought to bring up the power output from the alternator.
However, the voltage loss you've measured is certainly A problem.
POS battery power runs through several connections, fuse terminals, and switches, which are probably corroded and resistive, which is losing power to drive the alternator.
US the wire diagram like a road map to follow the path between Battery POS and the black wire at the Vreg. Each connection/device in the path is suspect for losing voltage. You can measure the loss by placing the voltmeter probes on either side of connector, fuse terminals, or switch, to find the worst offenders. But, you are probably better off just cleaning, lubing, and making sure each connection fits tightly and has a good grab on it's mate. If you do it right, the connection between battery POS terminal and Vreg will lose no more than 0.5V. If you clean the vreg contacts too, the alternator field coil should "see" a higher voltage and make the alternator work harder.
Because of the Dyna-s, your coils draw more power than stock. This means you engine will have to rev a bit higher to make more power than the bike consumes and still have some left over to gradually increase the battery voltage.
Which reminds me. All those connectors between the alternator and the battery terminals need to be clean, tight, and low resistive, too. And don't forget the ground path back to Battery NEG terminal.
Cheers,