I have never gamed at a con- the one time I was to GM, my session was cancelled- and so all of my gaming has been done with friends & family of some kind.
Just a wild guess. Over 100. Started in 1981, moved around a bit, but most of those were from my 6 years in the military. Lots of people PCS'd in and out, including me. And also ran a few Con or AL games.
If I include all roleplaying... I'm guessing I'm in the 300+ bucket.
I have had a group in junior High and High school. A group in college. Two groups in grad school. Four+ groups post grad school. That's a few dozen people...
But then there are the large larps, which have been 40-80 people affairs. The small larps. The EN World Gamedays (a tradition of a bygone era). The house cons...