I prefer Static anyway.. then adjust from there... via "experience" or "by ear" if ya like!!! Note: Not for Everyone!! but, we always did this with the DragBike, then check with Degree Wheel to see where we ended up.... so it could be Repeated!!!
BTW, I was Taught to remove the Condenser and Twist the Advance with Fingers.. tho once I found the "tool" I get more consistent results!!! Especially with the Dyna-S for some reason.

 

Nothing wrong with static, one has to just know there is a little room left for the dynamics.
Which way that falls is dont know.
In the end, i keep running it all ahead until I get the tinkles and start back off.
The factory setting is for factory engine anyway, and not much to do with a modded engine.

 

I think at this point- it may be time to open up the cam cover to have a look at the cam. Unless you are taking the cam out- you dont have to mess with the tappets.
take a look at the timing marks - see if they line up.
some cams (ie crane and others) had an option to press the stock cam gear on yourself- someone could have retarded or advanced the timing there.
you could always go old school and use a cam timing wheel and see if it matches the cams specs.

 

 

Me say no understand with caveman grunt, the little cam thing rotates has bumps on it to open the points.
Transparently it rotates right?
You should be able to pull the plugs and rotate the engine over (rear wheel) and watch all the kinetics.
Perhaps I just dont see the whole picture,?

 

try this first
rotate the engine around till you think its on the advance mark front cylinder

with a piece of 3/8 rubber hose put it over the front spark plug hole and blow into it > you should get resistance if not your out of time 180 degrees turn the engine over once around try again

needle nose small vise grips advance the points rotor it wants to turn in a clockwise direction

the advancer with the springs actually comes in clockwise and counterclockwise directions - confirm what way it turns for advance - counterclockwise is for flat side engines as the distributer turns backwards

 

Update---I pulled the cam cover and found that the timing marks on the cam, pinion, and breather are all dead- on where they should be. This leaves me scratching my head. The only thing I can think of is this: the motor was rebuilt and a new flywheel set was installed. I'm now wondering if the timing marks on the flywheel may be off (?)

I'll be putting everything back together tomorrow and begin to experiment with setting the timing mark at different places in and around the timing hole. As I had mentioned, I ground out the points plate adjustment grooves by about 1/4" and that brought the points closer to the high point on the lobe, but not close enough to get a test light response. So, once things are back together , more experimentation. I've bounced this off 3 good Harley mechanics i know and they also draw a blank--aside from the possibility that the flywheel marks must be off--ugh! If worse comes to worse, I can grind out the adjustment grooves more to get the points to open on the lobe. It sounds like a band aid but wtf, if nothing else works, that will.

 

Betting you have an aftermarket Points Plate...

 

As I mentioned earlier ... many are junk

 

My bets a trashed advance unit, fully half the bikes I've seen running like crap it was bad. Those $29 all in one kits were real popular and that cheap advance would last about a month.