Whole Leaf Tobacco and Leaf Only are probably the two most popular online cigar leaf vendors, and both have some excellent kits, both complete everything-you-need kits, and also kits with only the tobacco. They are quite economical for what you are getting, especially the tobacco-only kits. You can improvise most of your equipment. Just pick out a blend that sounds like what you want in a cigar. You will not be disappointed.
Just a tip. Lately I have used a lot of Ecuador-grown Habano2000 Viso that I bought from Leaf Only, and about half the leaves are actually usable for binder or wrapper, so a one pound stack of leaves gives me filler, binder, and wrapper, enough for I don't know, I guess about 20 to 24 cigars, for $24. I really never counted or weighed or measured. Blend, schblend. We don' need no steenking blend. Seriously this Viso is a bit mild for Viso, but still punchier than a Seco. Big leaf, good quality. If you want prettier cigars, get a 1/4lb sample of Nicaraguan Connecticut Shade Wrapper leaf to dress them up. Otherwise, the Ec. H2k Viso is rich and tasty, and burns well enough when used all by itself for the whole cigar. When you can roll a nice stogie for a little over a buck, and have fun doing it, you got a win/win/win situation.
Your first sticks don't have to be ugly. Just watch the videos. Get your binder into medium case and your wrapper into full case. (moisture content) and stretch them out good. Make sure the underside or veiny side of the binder and especially the wrapper leaf is up, the tip end of the half leaf is toward you, and the leaf's outer edge is away from you, and the side veins are more or less horizontal, side to side. You might try rolling your leaf out with a small rolling pin to flatten the veins a bit, then stretch the leaf out good again. Using a very slick rolling surface (I use a 24" x 24", 1/4" thick piece of plexiglass) helps the wrapper and binder leaves to cling and stay put when you stretch them, so you don't have to roll with one hand and stretch leaf with the other. You want the side veins to end up on the cigar running parallel to the axis of the cigar, so they can sort of disappear into the crevices between the filler leaves. Roll the bunch back and forth in steps as you roll, like three steps forward and two steps back, to press the veins into the cigar. Remember you want the wrapper to go on fairly tight and well stretched but not so tight as to constrict the cigar or burst open as the wrapper dries and shrinks while the filler absorbs moisture and swells.
Your first cigars won't look like Opus X but they don't have to look like Backwoods, either. But you and I are in agreement in that how it smokes is more important than how it looks, unless you are just showing off at your local cigar store smoking room. Then again, smoking an obvious DIY stogie actually gives your Davidoff or Romeo smoking neighbor cause to be envious, even if he won't admit it.
A lot of guys who roll without molds, roll the bunched and bindered cigars up in paper to settle in a bit before applying the wrapper. I tried it and I don't see the difference, but my rolls are usually perfectos so it's a different can of worms from rolling parejos. (standard straight sided cylindrical cigars, that is.)
