WT Wizard, smoking a cigar shouldn't involve inhaling, much like smoking a pipe. The few times I accidentally inhaled if felt like a mule kicked me in the chest. Cigars are to enjoy the flavor, the time it takes to smoke one and the experience.
As far as getting the best you can afford, absolutely. It's no trick to find a good cigar for $7, a really good cigar for $10-12 and a great cigar for more than that. The trick is to find a good cigar for $3 and a great one for $5 ;)
Same for Scotch (strangely I just got back from buying some at the liquor store and stocking up on cigars yesterday...). Once you have good scotch and good cigars, you can't go back. I am lucky enough to have a cigar store nearby (JR) where you can buy at about 40% off regular price if you buy in quantities of 5 or more and have liquor stores nearby where I can get Macallan in 1.75 litre bottles.
Sadly, I can afford enough good quality of both to abuse whenever I choose, although I rarely choose to abuse.
Having said that, it's almost time for American football, beer, whisky and cigars.