dougajmcdonald
Club Champion
Handicaps are always the most contentious subject about golf. Its really difficult to get it right unless you play about 20 tournaments in a season in my opinion. I manage our society handicaps and nobody is ever happy.
In answer to your question I remember doing a poll on this last year which was pretty interesting
http://forums.golf-monthly.co.uk/showthread.php?74232-Handicap-How-often-do-you-play-to-it
I see your logic here but I have to disagree on a slightly pedantic note. As someone who played > 30 comps last year I think getting a handicap right is down to how consistently you're playing.
Consistency can be gained in many ways, playing many times as you mention would probably indicate more accurately where you are, but if you're new to the game and improving quickly, playing many times won't bring your handicap down quite as fast as you improve (it will in general, but it will always be a few rounds behind).
As a result, I think it's only when you settle on a swing or reach a point when your rate of improvement slows and then you couple this with regular comps to ensure that your performance has normalised, that your handicap will be 'right'.