Cigar Cutters
There are many styles of cigar cutters. I prefer the double bladed guillotine cigar cutter because they are long lasting and cut evenly. Make sure it can accommodate most ring sizes. Other people prefer a punch or bullet cigar cutter that just puts a hole in the foot of the cigar. These are especially helpful with short filler cigars because the tobacco is loser and a smaller hole means less tobacco in your mouth.
The first thing you should do is closely examine the "head" of the cigar - this is the closed end that needs to be clipped. Almost all have what is called a "cap" - a bit of tobacco leaf used to close of the end - you should be able to see how far down the length of the cigar the cap goes by inspection. Typically only a 1/4" - 3/8" or so; sometimes much less, and on figurado shapes sometimes quite longer. Anyhow wherever the cap stops is your cutting limit - cut beneath the cap's line or even too close and your cigar will start to unwravel, and as you pointed out this is extremely unpleasant. Try to cut the minimal possible while trying to open approx. 75%-85% of the cigar end's surface area. Sometimes this means a cut as little as 1/32" down, where other times almost 3/8" - it depends entirely on the individual cigar's roll and cap construction.
The single bladed cheapie cigar cutters that most newbies are given or buy for $3 typically do a very poor job of clipping the cap, and result in crushed, split, and tatterted cuts. One thing to keep in mind when using a guillotine cigar cutter is to line up your cigar at eye level and to them clipped it quickly and decisively. This method gives satisfactory results nearly 100% of the time.
Many smokers swear by the .44 Magnum cutter which is a relatively inexpensive punch that is easy to use, makes a perfect round opening, and completely bypasses the problem of how much to clip. Crestmark also makes a nice cigar punch that extracts the cut cap from itself.
V-Cut clippers are also available, and a few cigar smokers think this is the only way to clip your cigar. You don't have to worry about the caps length using this type of cutter since you rest the cigar against it, and it "automatically" takes out a v-notched shaped bit of tobacco of the same size everytime. These cutters typically work better on some sizes than others, depends on the size of the v-notch blade.
Cigar scissors are elegant, but they are difficult to use. Some people use x-acto blades, swiss army pen knives, their teeth, and so on. How you clip your cigar is a matter of what works best for you. Just keep in mind where the cap ends and you should be fine.
Source: Bob Curtis, Internet Cigar Group
Double Blade Guillotine Cigar Cutters
It is the same concept as the guillotine, but the two blades provide a more precise cut. You will also need to cut with force, but some sophisticated double blade cutters like the XikarŪ Xi Cutter have a spring mechanism that ensures a clean cut every time.
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Cigar Punch
The punch cutter will cleanly cut a small hole on the head of the cigar. To cut a bigger hole, you just need to insert the punch several times until you get the desired width.
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Cigar Scissors
Just like a double blade cutter, the cigar scissors cut off the cap of the cigar.
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Cigar cutters selection
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