Having a tool to check the compression is a good idea. Only thing is that normally a compression tool has a check valve that can trap the air from the pressure pulse of the piston in the gauge so you can read it properly. Then there a small release valve to evacuate the air so that the pressure gauge needle can go back to zero. If you don't have the check valve, the gauge needle will bounce about and you will not be able to read the correct pressure.
Regarding the oil reading, go ahead and check the oil pressure at the location you are referring to. By default oil pressure at this location will be a fraction of the pressure near the pressure release valve. The reason for a large drop in pressure at the head is because the oil is going to the main bearing, to the big end bearings, from there it is travelling to the small end bearing or gudgeon pin, then it is sprayed on the cylinder walls. At the same time, a portion of oil is directed via passages in the block and head for it to reach the camshafts etc. So in effect the head is the last place for the oil to reach by that time a huge pressure drop has already occured. Anyhow, all I can say is that if you get a health pressure at the head, then surely the pressure at the gudgeon pins should be pretty good too.