John,
I really don't mean to pontificate. There are a gazillion ways to do this stuff that work just fine. A very high-case leaf will stretch smooth over a smooth bulk.
In many Caribbean cigar factories, the experienced rollers are paid more than the other workers. So some of the factories have lower-wage people sitting at what looks like a flat "ironing board" press, like the ones that used to be common in commercial laundries. Here they press each leaf. This allows the rollers to wrap cigars faster.
My view of this process of pre-pressing the wrapper is that it is an economic decision to increase the productivity of the higher-paid workers. For one-off hand-rolling at home, I think it's a step that isn't necessary.
When we watch those videos of cigar rollers in factories, they make it look easy, because somebody (or bodies) else has already done part of the work. The most useful video I've ever watched was one that FmGrowit posted on FTT back in July 2011, that shows an older Cuban woman rolling cigars free-hand, from scratch, as a demo during some sort of German conference. She moves "slowly," deliberately, step by step, then hands a finished cigar to one of the attendees. The pearl of her actions is how she patiently hand-compresses the bulk, while adding scraps, until it is as smooth as a chair rung. In wrapping, she often backs-up, gives an extra tuck into the bulk, then proceeds, apparently going by the compressive feel of the bulk beneath her fingers.
I watched that one many times, as opposed to those with the partially undressed bimbos rolling pre-setup cigars on their thighs, while flirting with the camera.
Don's all-time best cigar-rolling video:
http://www.youtube.com/watch?v=pYh2FOObW6E&feature=related
(I just watched it again twice. Damn! It's good.)
Bob
EDIT: I just noticed for the first time that her glue is so thick it's like an ointment.
I would kill for my Mom's old wringer washer.
