There are a few variables to look at:
1) How viable is the yeast you're using? (depends on storage temp, age, ect...)
2) How much yeast do you need for your gravity?
3) How much yeast do you need for your type of yeast? (ale/lager)
4) Do you want esters caused by under pitching? (good for some styles, not for others)
5) Are you willing to risk off-flavors caused by under-pitching/over-pitching? (this seems random to me, but does happen)
6) And ultimately: Do you want good beer, reproducible beer, or to "just make beer"?
When I first started out, I got lucky and even though I under-pitched I had good beer most of the time.
When I wanted to reproduce my results... the next beer would always taste good, but have a different profile than what I did before.
Now that I have nailed down my procedure for pitching rates and other yeast practices, my beers are much more reproducible.
People tend to ignore yeast practices, but in my experience, you can have 2 identical grain bills, the same temp, same everything else, but if the yeast is different (in amount, type, generation ect...) you will get very noticeably different beer!