Condenser is in front of the radiator, the evaporator is in the dash.
R134a will leak through orings and hoses after many many years very slowly. Your AC wont just be blowing cold today, then in the morning nothing....you will lose cooling capacity and the compressor will be short cycling. That is the sign you are GETTING low. Too low and you wont trip the cycling switch and therefore the compressor wont engage.
If you suddenly dont have enough "freon" refrigerant then maybe your leak just got worse.
And yes its a great idea in the winter to run the AC to circulate the oil and keep everything lubed. Turning on the defrost in the winter usually does this also unless the ambient is under ~35 degrees and the compressor is disabled by the PCM.