Please know that not all principals are paid as highly as many of you believe--or maybe you know(I know in some urban areas the pay level is much higher), but I don't know of any in our area that make even close to $100,000. I don't think our superintendant makes that much. My husband is a principal and puts in a lot more hours than many others in our district who make a lot more than him(coaches).
In my case(a middle school) I'm glad to give the $5 for each one because I'd probably spend more on something if I bought something myself for them and they would appreciate the cash more anyway. With DH being a principal--I know they aren't exactly rolling in the dough and appreciate the sentiment.
I don't feel the need to supplement my principal's salary because "they really don't make that much." I don't know of any district where a principal makes less than a teacher. Coaches have extracurricular positions which increase their overall salaries.
The bottom line is that any boss depends upon the performance of his/her staff to make his/her own job performance acceptable to his/her superiors. Therefore, I feel that a gift to members of a cooperative staff would show appreciation. As I stated in my original post, unless a principal has been exceptionally kind or considerate, I don't understand the rationale behind a gift except "kissing up."
As for the higher salaries in urban areas it would be in line with the higher cost of living in these areas. I live just outside Manhattan where a very modest house in a middle class town for $500,000 is a bargain. Rent for an equally modest 1 bedroom apartment is around $1500. $100,000 doesn't mean the same standard of living here as it does in most of the country.
Lest anyone think that I am just "anti-boss," I shopped last night for a sterling bracelet for the office manager at my DD23's part time job.She has always been appreciative,compassionate and generous to DD who is also a full time grad student and teacher assistant. I made sure that she had a gift to thank her for all of her kindness.