I always set the timing when at max mechanical advance.

Unplug the vacuum advance canister.

Start the motor and rev it until the timing light shows no more advance.

Set it at 34-36 total (my 440 loved 36).

I've never liked setting the initial and don't care much for the vacuum side either. I usually either plug the vacuum hose with a BB (for the resto look) or elimnate the hose altogether.