In the early days of TR chip burning, everyone made aggressive timing chips, in order to make more power. That was just how the old school hot rodders had always done it. However, over the years, and with much learning,,, the modern approach seems to be; running less timing and more boost. We now have the ability to readily get more fuel into these things than we could ever burn, therefore it allows us to lower the timing and crank the boost. I've had numerous conversations about this in recent times, and the opinions do still vary somewhat, however I see the faster street cars running less timing and more boost, consistently! And yes, you are absolutely correct in your detonation assumptions.
It all depends on your entire setup, as to how much timing you'll want to run, however I tend to lean towards staying conservative on the timing side. That stems from the early days of popping head gaskets like they were made of tissue paper, when running aggressive timing chips,,, and then never popping another with a 20-22* chip. Just my opinion though...