On the subject of learning to roll your own cigars, the first one will be a landmark event. (Post a photo of it in the Pics of Your Sticks thread.) I found that it takes about 30 cigars to become adept at reliably rolling a cigar that draws well. Don't give a moment's thought to what it looks like. That will just come naturally with practice. Whole Leaf Tobacco's cigar blending kits are a reasonable place to start, and provide combinations of leaf that will make enjoyable smokes, regardless of the kit you choose.
Your skill will increase most rapidly if you roll one, then smoke one. I suggest not starting out with a mold, as that adds an additional layer of challenge in getting the draw right. Just free roll them.
Bob