Run your A/C once a week and you'll reduce the chances of having problems with it or having any concern with adding oil. Running the A/C keeps the seals lubricated by spreading the oil.
If it puts out cold air there's no need to try to check the A/C oil. There is nowhere for this oil to go and it doesnt get burned up or used up.
The only way to check how much oil is in there is to discharge the system (hopefully legally), and then drain the oil out of system and measure how much was in there. There is supposed to be 2 or 3 oz i think. And then you would have to add some oil back in and repressurize the system with the right quantity of refrigerant. And there's no reason to do all this unless the A/C had something wrong with it anyway.
So i'd only worry about the A/C oil if it stops blowing cold air and might need a refrigerant added. And even then you would probably see signs of oil leakage somewhere on the compressor. This place sells oil checkers.
http://www.es-refrigerants.com/produ...19/details.asp