Hey Eric -
So if I understand the question, you are saying why is it ok to value a live $1 chip for $3 and a live $5 is not $15 and a live $100 chip is not $300? Or are you saying why is a live $100 chip not worth 37 live $1 chips? Guides are just guides... They are based on the information that the author knows about the scarcity of the chip (supply and or ease of acquisition) and demand. I use them to gauge scarcity knowing they are only as good as the author's info, and provide me guidelines for proposing a change.