Steven, you say you have compression on 1, 3, & 4, --but no compression on #2. When it is running, do you hear a"popping noise" out of either the exhaust or carburetor?
While Joe and I think alike on this, one thing that is critical is re-torquing the aluminum heads until they 'settle in'. While you only specified it was a finned H/C head, this may apply here too.
Might I suggest you do a cylinder leak-down test. If you do not have one, but do have a way to pressurize the cylinders, I would put an air hose on it with about 35#-40# of pressure and listen for leaks. If you need an adapter, they can be purchased, --or fabricated by welding a quick-change air fitting to a "hollowed out" spark plug.