I adjust mine at least once a season - but if you have done any work up top, you should do it more often.
The normal thing to do is when it's audible - but with the yamaha OEM clatter design, it's hard to tell when it's louder than normal.
As for holding the square tappet - I use a set of needle nose vice grips - this lets me get a good grip on it with just enough space to get the 10mm wrench in there to snug her up.