Any beginner of the cigar smoking should start from mild to premium. This is to allow him to taste a variety of them before settling on the taste he want at a cheaper cost for they are available in singles than boxes. Another reason than the price and the quantity available is that the more expensive cigars are stronger and could be hard on the new smoker. 

Also because he is not experienced in cutting there is no much loss if he cuts wrongly. So the mild cigars should offer practice before going for the premium hand rolled cigars.

Another hint is to inspect the cigar by squeezing it to check on the hard points which could affect you draw. You should also check the wrapper to ascertain that it is not cracked or discolored. If you notice are any signs of above defects request the tobacco vender to replace with another that has no defects. Any reputable vendor will replace the cigar for he knows the importance of smoking a perfect cigar. The beginners most are off the shelf smokers the at this experimentation stage they do not require the humidors.

In the case of having bought more cigars than need for you several days’ consumption; you could use a cellophane wrapper to preserve them to keep them fresh till you smoke them. Obviously the beginner does not have the necessary cigar accessories so he would sometimes need improvisation. You can cut the cigar cap using your teeth or any other possible way as use of the available blade like the scissors or the razor blade.