SoCal got it right, if we could eliminate all guesswork and know all variables spot on, we could use Dynamic Compression and get everything right, every time. We could make excel sheets with automatic calculators that give us every detail and allows us to play around with the variables we have control over, to show us what our Dynamic Compression is. (You'd still need to know how much dynamic pressure each cam profile and parts combo likes best).
Sadly, we'll have to make do with Static CR, because that is the only hard, undisputable dataset we have, assuming we can measure our parts adequately.
http://www.johnmaherracing.co.uk/enginecalc.htm
Use that to play with the abovementioned variables, and see how changes in one thing affects Static CR.
Now, since things are pretty much the way they are, we need to stick with static CR in our calculations. The most vital "variable" then is the engine builder's experience. With time, you learn which cam likes which static CR, under what kind of other circumstances. You can't beat experience.
If you are really deep into it, you will know to read new (to you) cam profiles and determine the best CR for that too, without ever assembling anything or running the engine on a dyno.
Even so, you always need to leave a little bit of safety margin, more for the street, less for racing (Where every HP counts and rebuilds are frequent).
Race engines are generally built to closer tolerances, more accurately, and with better tools, so you can safely (?) narrow your safety margin to harness the last mangy pony (no pun intended) hiding in there.
Race engine building is more of an exact science, stock rebuilds and mild street engines are easier because you can rely more on 'guesswork', just err on the safe side and call it safety margin
Then there are perfectionists who rebuild their lawnmowers to race tolerances, with computer assisted design and optimization, blueprinting and balancing etc... just because they are fascinated by the fact that they can

Or they are too proud to half-ass anything they do. Or they are just bored out of their minds.
It gives you a nice warm feeling of accomplishment (and superiority) when you can tell your neighbor that your 5.0hp briggs&stratton is now actually a 5.025hp.
Sorry, I guess I got a little carried away
Jan