If I remember correctly, the proper procedure for checking the A/C output is inserting the thermometer in the center vent, recirculate, fan set on high, engine at 2200 RPM. Ideally, the temp. should be around 40F. On a hot day (100+ F, high humidity, etc) a perfectly functioning A/C system may not be able to put out air colder than 47-50F.
I haven't spent a whole lot of time in the business, and the time I did put in was almost 5 years ago, but I have never seen for myself, or heard of, an automotive A/C system putting out air colder than 35F.
Running the A/C system once in a while for a few minutes in the off-season is an excellent idea.
However, owners of late-model (model year 1995 and up, I believe) vehicles do not need to perform this function, since A/C compressor engages every time the defrost is on.