With the compressor off, both sides will equalize. So it's normal that whatever pressure you see in the high side will be the same in the low side at rest.
The charge is measured in weight, not pressure, so you really can't tell if the system if actually "full" by just a pressure measurement, all though you can get a good idea.
As you noted, since the low side goes very low when the compressor is on, that indicates a low charge. I wouldn't exactly say it is "empty", because the compressor does come on and there is pressure in the system, but it sounds like the charge is definitely low.
To answer your question about the vacuum pump, you will never pull all the oil out of the system with the vacuum pump, it is not possible or necessary.
With no leaks, you should be able to pull the system to very close to -30inhg. If it won't go that far into vacuum, there is a leak. It should hold this vacuum for a very long time. If it does not, there may be a leak. I say MAY be a leak, because I know my recovery machine won't keep a vacuum on the system for a very long time at rest.
If it is determined there is a leak, Scanner Danner has shown us that you can evacuate the system, pressurize the system with air (I like 100psi or more), and monitor the gauges. There should be no appreciable loss of pressure. If there is, then you can locate the leak with soap and water.
"Ground cannot be checked with a 10mm socket"