I started understanding flavors,tastes,sinus,and pallette related stuff on wine tours.I have always been into wine and coffee and tried to learn how tasteings are done and how they find such intricate flavors.On my quest,I found craft beers and again liked beer again.
I started on the low abv and lighter beers and worked my way up to barleywines,scotch ales and porters and what not.I then went to gins and vodkas.Then on a hunch and a craveing I tried some decent 12yr old scotch and loved it but found it burned my stomache too much which is probably ulceris.
What I did in the beginning was on the rocks with water then went on the rocks only but lowered the ice amount after some time to alleviate the watered down taste.In the winter I do it with no ice and a splash of water.
I am working on bourbans and american whiskey but usually only in the winter.Its alot harsher but with all spirits I can indeed pick out flavors and pair with a good cigar.
Try Glenfiddich 12yr old,very smooth and fruity for about $35 a bottle here.
Or maybe on the cheaper side and usually on sale everywhere today Dewers 12 yr old,the gold round container.also smooth and fruity.
The wife loves scotch but still waters it down too much but she has worked out kinks in her drinking habits,it just took some time.
I agree with ABV,stay away from islay or other peaty scotches for now.
Just too mention I do cognacs and brandy too but find them too sweet to enjoy for an entire night.
As mentioned above previously,take your time,sip,and like a good cigar try to slow it down to almost a meditational experiance and try to pick out flavors and things you notice.Doing so will cause relaxation and this is where the "I need a cigar or a scotch to relax" comes from.
Enjoy!