Does it piss them off if. . .

[razor]

does it piss off sites if they are pinged with only 5 packets sent out to test there speed and would it be okay to put it on one of my websites

[jvv]

Probably not.

[Chicken]

You'll want to at least ping from different locations, not just yours. From 5 places a few times would be better.

[Koolguy]

Also note the fact that most sites don't even record ICMP traffic.