the shims' job is to correct valve lash from the cam lobe to the lifter bucket, they will not have an affect on spring pressure to keep the valves seated.
Usually piston rings develop blow-by before valves start leaking. Try a bit of oil in the low cylinder to help the rings seal up, that should bring up your specs during compression testing.
EDIT: saw you checked the thermostat
How long did it take for the hose to deflate? Should be the normal few hours and not overnight.
What temperature is your thermostat? It should be 88*C (~195*F)
The thermostat is a one-way valve that would take forever to open up if the wick was facing the wrong direction, plus the water pump only circulates one direction and works best without obstruction
Think about how the head gets hot fastest, the wick is installed facing the head to open up fastest, and once open it allows the water pump to push some cooler fluid from the rad into the water neck past the thermostat through the head and into the block, past the pump and back to the rad to cool again.
Is there something wrong with that logic?
He just fixed a headgasket, ten minutes to check can save him hours of work and hundreds of dollars.