2 expensive wines, how did I fair?

[Peter rotelle]

Thank you all for your responses, my first time on the site and look forward to learning more about the world of wines!

Did I over pay? Of course, its Nantucket. I guess my questions should have been better defined. Are these wines expensive has-beens and the sommelier pawned them off on a sucker like me? The first bottle, Mazis-Chambertin Philippe Naddef, my wife and I both loved (and thats all that counts to me). The second, Masseto was excellent by my taste but thought differently by my wife. I would like to source both so I can purchase for home consumption. Any thoughts where I can find them?
As for Cioppino's - Tracy and Susie have a wonderful restaurant with very reasonably priced wines - I must agree.
Toppers boasts about winning Wine Spector Magazine's Grand Award (only 93 restaurants worldwide hold this honor). Is that truly a prestigious award? By the way the food, was in the top three I have ever eaten!!!!
I look forward to your thoughts and suggestions.

PS What is the tipping etiquette on wine? I only tipped on the first bottle, and to my waiter not the Cellar Master. Sould you take care of the Cellar Master (he was the one who kindly helped me pick my selections)?
Please advise........