The compressor should not kick in if low on refrigerant. It is protected by a low pressure switch, it is possible for the switch to go bad and thus ruin the compressor. The compressor is not lubricated by the refrigerant, it is lubricated by PAG or ester oil; in older R12 systems it is mineral oil. While most oil stays in the compressor some oil is carried by the refrigerant through the system, when there is a refrigerant leak you loose a small amount of oil with the refrigerant. If you loose enough refrigerant and do not add any oil back into the system you will eventually burn up the compressor.
If you have had the vehicle since new and know there hasn't been any leaks before you can safely add refrigerant to it without worry. It is were you have had to add refrigerant on a regular basis is when you should add some oil. How much is pretty much a guess, usually just an oz or two at the most. Be careful not to add to much oil as it is a non condensable and will effect the cooling capabilities of the system.
When adding refrigerant a general rule of thumb for the high side pressure is 2 1/4 to 2 1/2 times the ambient temp. So if the ambient temp is 80* the high side pressure should be 180 psi to 200 psi. I want to make this clear this is a general rule of thumb and different systems could be higher or lower than this. The low side should be between 30 and 40 psi. Again a general rule of thumb. Overcharging the sytem will also effect the cooling capacity of the system.
Another way to charge the system is by vent temps, put a thermometer in the center vent and monitor the temp as you add refrigerant. Add only an oz or so at a time. Let the system run a couple of minutes until the system stabilizes, measure the temp. Once the temp no longer drops stop adding refrigerant.
You can also measure the inlet and out temp on the evaporator. There should be a 10 to 15 degree difference between the inlet and outlet.
Yes air conditioning work is expensive, make sure you go to a reputable shop. There are a lot of shops that have a guy with a set of gauges and claim to experts.
Remember if you have to add refrigerant you have a leak, find the leak and get it repaired. There are dyes that you can add to the refrigerant that will show up under a black light. There may also be an "oily spot" were the leak is, but may not always be the case if the leak is small.