with the 429 I have it way up, i am at 22 degrees initial 40 total. No problem. With the CLeveland I could only go 16 at the most without spark Knock. But I had to go with a bigger battery. it only had a 450cold crank battery in it. I went with 1000 cc no problem.
I'm running 14* initial & 34* total, all in by 2500. No starting problems.
5.0 shortblock, Aluminum TurboSwirl GT40 heads, and E303 roller cam 282*/.498. The E303 likes 14/16 of inital timing (according to the late-model guys), and the heads are "fast burning", hence the seemingly low total, but that's where it makes best WOT power.....I do also run vacuum advance for part-throttle response.
I was 16* initial - the car started fine, but had some run-on when shutoff.
I have a 351w with it bumped up to 12 initial. Any higher and it pings and loses power with the 10.7:1 compression. I also had to limit my centrifugal advance to about 30 degrees total advance, any higher and it will ping. I also have vacuum advance too. That will advance the timing another few degrees or so above the 30. All in all, it has only taken me a couple of months to re-tune my distributor so that my engine will run up smoothly AND not ping.
i posted a question about five speed behind a big block and i tried the search just as you suggested and it came up empty. i went back a year and still nothing. since you seem to be the post police maybe you could give me a couple of links to those answers. thanks