These motors are bone simple, don't make them complicated.
The cylinder and head can go off and on a dozen times with the same gaskets if you don't damage them.
This is the beauty of these engine, you can tear into them and do your modifications one at a time.
No water leaks, a simple quick test for gasket leaks and you are off!
--- Raise the exhaust a bit, put it back together and try it
--- drill a small boyeson, and try it, then try larger,
--- drill a boost port in an old piston, then try it
--- put a spacer on the intake, then try it
--- etc, etc, etc, back to back testing, not 5 mods at once.
This is the only way to learn and these motors offer this opportunity.
So don't make the gasket thing too complicated. It is really very simple.
Once you have it in final form, and don't plan to open it up again, yeah, new gaskets and careful warm up.
Don't fear it man! Steve