I agree with BubbaC on all aspects!

It can be almost a hobby...trying to find 'your' perfect cigar to match with 'your' ideal
whisk(e)y...
One of my favourites...
Avo Uvezian Robusto Tubos + Wild Turkey Kentucky Spirit(from '94)
The Avo is quite mild and has a creamy flavour and the wild turkey is very toffee and caramel...the 2 go together just fantastic!
One piece of valuable advice...Invest in a good humidor!!!
I also believe that the glass or acrylic top humidors are great but as long as they are kept out of the sunlight!!! Don't put it near a window.
I actually have 4 humidors
One for flavoured cigars - You must keep these seperate from the natural unflavoured cigars!!
One for 'cheap' cigars...basicly one's for guests that haven't had a cigar before and would like to try one and just in general.
My personal one...got some of the best cigars in this one, Cohiba Esplendidos, Davidoff No.2's(Cuban) and my Avo's(nearly out of these

)
And I have an old one which I am not currently using.