I agree with the cut being important. I usually use a punch cut to get the small hole in the end of the cigar. Usually when I'm around others I use the double guillotine because I am going to be involved in things other than relaxing and searching for the subtle changes in flavor.
I would suggest Torano cigars. They are good quality and not top shelf prices. They also have a wide range of strengths.

If a cigar tastes good smoke it, if you no longer find it pleasing give it the heave ho. Keep a log or journal of what cigars you tried and what you thought of it as you smoked it. Learn all you can about how it is made and where the different tobaccos are from. When you buy pick up a 5 pack or even 3 of the same kind. Then smoke one right away and log it. Let the others sit in the humidor and try it in a few months or if you can longer. Then compare. Smoke the second one write down your notes then reread your notes from the first one.

Cigars should be enjoyed not tolerated!