Slo, from the couple builders I have talked to and what I have read a good safe squish should be between .040 and .045. Under .038 you really need to know that all your other parts are in damn good shape if you expect your RPMs to be on the higher side. You really can't measure the true amount of streth in all your parts at high rpms. So to keep safe you should try to stay above .040. So if you have a stock head and you want more compression then what shaving down to .040 can get you, you should have the head rechambered. If your motor is stock or a very mild port meant for more of a low to mild range then yeah you could maybe go a little tighter with for squish.
Here is my run down:
Stock motor looking for a compression bump, shave the head down to .040 squish
Stock motor looking to run race fuel, rechamber or cool head
Ported motor looking to run either pump or race fuel, rechambered or cool head
(I think if your spending the money for a port job at least have the builder rechamber your head to his specs)
If you have an idea your going to possible be changing setups a few time go cool head.
It seems that the cooling between the two is pretty close with some saying the cool head helps and some saying it doesn't.
The hp difference between cool head domes and a rechambered head are about the same.
So I think a lot of it comes down to, are you going to stick with one setup or do you have a feeling your going to be doing some upgrades and changes that will require head changes.