"Inquiring minds want to know, what qualities are generally attributed to cigars of worth? "
Hmmmm....That's a good question. Let's start with cosmetics....
A nice uniform stick, with a clean square cut and a smooth looking wrapper. Little green sunspots are always a bonus, cause they are caused by droplets of water which dried on the wrapper and as far as I know are only found on the "Forbidden Fruit" A white powderly substance on the wrapper is called "bloom" and its OK. Small holes in the cigar are very bad and are typically caused by tobacco beetles, and if you pull one like this out of your humidor, it's time to act immediately.
If you gently squeeze a good cigar it should feel firm, with no soft or hard spots along the length. It's shouldn't crack or make crunching sounds, but feel resilient. A too dry or too wet cigar will also reveal itself this way. A good even roll is key to an even burn. Even a high quality cigar loses appeal when it burns unevenly and keeps needing a relight to try and even it up.
Speaking of burn, a good cigar should burn evenly and the ash should easily grow over an inch long without difficulty. A cigar that loses its ash quickly is typically rolled from short pieces of tobacco, clippings, floor sweepings, or even <shudder> machine rolled shredded tobacco. The ash color is not a giveaway of quality. A light ash is indicative of high magnesium content in the soil. Typically Cuban cigars have a darker ash. A good cigar should only need a puff every 1-2 minutes if well lit. This allows the smoker to savor the cigar and not feel like he/she is being rushed as to keep it going. It also allows you a chance to really enjoy the subtlties of the flavor, instead of that hot burnt flavor that comes from smoking one too fast. Don't stub a cigar out. Let it go out on it's own, put it into a commercail snuffer, or if necessary for the sake of speed, cut off the coal. Stubbing it out makes the residual aromas much stronget and harsher....
Flavor, that's the $64,000 question. Good tobacco like good wine has a whole litany of flavor descriptions. Spicy, nutty, chocolate, coffee, earthy, etc. The thicker the ring (diameter) the wider the variety of tobaccos that can be used in the blend, and the longer the cigar, the more the blend can be varied down the length of the cigar. That's why the best cigars are the fattest and longest, because they allow the roller to demonstrate their ability to mold the flavors of the cigar into an experience that changes as the cigar is smoked.
Different growing locations have different strength and flavor profiles. Domincans and Mexicans tend to be lighter, with Honduran and Nicuraguan medium to stronger. Cuban call fall anywhere along the spectrum. Non Cuban brands will many times be a mix of tobaccos from several regions. Watch out for a high Ligero content in a cigar. Turns a smoke into a real punch packing heater which could easily make your head spin and your face green
For me, a Hoyo de Monterrey Double Corona from Fidel's Island is as close to the ultimate smoking experience one can have. Be prepared to pay upwards of $25 apiece when you can find one, and sadly, not typically on these shores. However, in Canada or Europe, one can find them with some effort. Then put aside 60-90 miutes of your time when you aren't rushed and can really enjoy it. I also like a glass of some fine beverage, some vintage port or a good single malt or upper level brandy. Light that heater up take a sip, and for a little while you'll feel like the King of the World...Heh, becareful when you stand up afterwards, too....
Oh and one last thing. It's widely held that a good cigar isn't worth smoking until its been laid down for at least two years in a proper humidor. This gives the tobaccos a chance to age and blend together. The well aged cigar will also shrink, making the label loosen. A loose label on a cigar from a reputable maker is a sign that a cigar has had a chance to age properly, and if you are lucky enough to find one like this at your tobaccanist, buy it and smoke it right away if you feel like it. I have some Cubans a friend gave me in 1996 that are still sitting in the bottom of my humidor.
Hopefully I will have a good enough reason to pull one out and fire it up soon....