I cannot say that I am much of a NV man, but under $60 it is pretty hard to go wrong with VCP, Taittinger, PJ, or Roederer. I will say though, if you have not tried any of the offerings from Nicholas Feuillatte, you should definitely try some. For about $60 though, you should also try some of the more obscure grower champagnes, some of them are far better than their price tag would suggest. If you truly enjoy champagne though, it is worth a foray of sorts into vintages, even the VCP, Pol Roger, or Taittinger vintages can be had around $65-100, and the vintage bottles just below their prestige cuveé is still always pretty good.
Aj60s, perhaps it is just me but I would not recommend drinking champagne with a cigar, as I feel the cigar ruins your palate for champagne. That notwithstanding, out of the wines you listed I would most definitely go with the Winston Churchill, but the 2000 is a great vintage of Dom as well, and to your question about more expensive champagnes being worth it: absolutely. With champage your really are rewarded for spending just a little bit more and buying one of the better champagnes from a good vintage. In the price range you are listing, I think you should also consider Krug, the grand cuvee, and VCP's La Grande Dame.