It's an efficiency thing...
You want the squish band to push as much of the charge into the combustion chamber as possible, most of what ever is leftover in the band doesn't get a chance to ignite, so is more or less wasted. Most of the velocity issues with too tight a squish are due to wide bands that aren't possible in relatively teeny chainsaw motors.
I read a lot of different numbers for minimum effective squish, somewhere around .040-.060" is typical, but that is likely dependent on bore size and/or band width and most published info seems to deal with larger bores. So who knows really?
If you go from .015" to .030" it's doubling the loss, and the squish is such a large percentage of the bore size in these little motors....
I'd enlarge the combustion chamber before I'd deepen squish if I wanted the most out of it.
As far as detonation goes, supposedly with these small bores it just isn't an issue at any practical compression rate, even with 87 octane.