I went through that with a 340, and now with a 445. What works is;start initial around 18, play with it, best rpm, best vacuum it won't kick back, lock down, and write it down.
Rev it, and check total, write it down. Now, go find a hill, and lug it up the hill; no ping, more advance, until it pings. Back off 2 degrees, and go home and read the total.
Now you have changed the initial, so; timing light the total, at rpms, then from that #, subtract the original initial # it likes.
Then adjust, however, which way depends on make, the limit in the distributor, to have that much advance. Then reset at initial; total should be correct.
And the total it wants constantly changes, with gas, weather, etc.
Example; the new 440 today, wanted more than 36, but dist had 18 in it. Putting more total in it, raised initial into kick-back. Re-curve time.