When looking at how well a cigar is made it is all about the feel of the cigar. When you pick up a cigar you want to hold it with one hand and then firmly feel the cigar with your fingers from one end to the other. You want to see if you feel any hard or soft spots in the cigar.
Ideally it will be consistent through out. It will take some getting use to be a proper cigar will be neither too hard nor too soft, or inconsistent as these conditions will cause the cigar not to draw properly.
How the cigar was aged and stored is very important when looking at the condition of a cigar. Good cigars are aged for several months, and better ones for years. During that time the finest cigars are stored at a humidity level of 70% RH, and kept at a constant temperature, optimally 70º F.
Causality (cause and effect)
This is the subjective part of classifying a cigar as everyone has different tastes. As with wine I always tell people it isnt the rating, or the price of a wine that makes it a great wine, its how much you enjoy the wine that matters. The same is true with cigars. What you will want to look at when smoking a cigar is if the flavor builds as you smoke it. Can you taste a variety of flavors giving it complexity? Does the cigar calm you as you smoke? How does it make you feel? How did it burn? Did it draw properly?