CR,
The best way to learn cigar rolling is to have a decent quantity of suitable tobacco at hand.
Although I use damn near every variety as a wrapper or binder at times, having true wrapper grade leaf makes the process much more forgiving. For smaller cigars, I often do not use a binder, but again, a binder makes all cigars easier to roll. It's not unusual for me to stem a single wrapper leaf, use the nicest half for the wrapper, and flip over the other half for use as a binder. I would suggest ordering some of FmGrowit's shade wrapper. For filler, order some of BigBonner's Maryland 609 and some 2011 Burley mid-stalk. Add a small strip of stronger tobacco to the filler to create different flavors.
The filler should be in low case (barely flexible). I cut my filler to length before rolling it. This wastes far less leaf than the factory approach.
The binder should be in medium case (dry and quite flexible).
The wrapper should be in high case (slightly damp and stretchy).
When I use glue, it's just a thick goo made from fruit pectin. For my own smoking, I never use any glue. If you roll a cigar that is too tight, by not using glue, it's a simple matter to unroll it, loosen the bulk and bit, then re-roll the same binder and wrapper.
A cigar mold is no help in rolling a good smoking cigar. It simply promotes rolling 10 bad cigars at a time, and can be truly discouraging.
Roll one cigar. Smoke it before rolling the next. This will allow you to quickly zero in on producing a nice draw. Don't take a photo of your cigars until you've made at least 100. Aim for functionality. Impress your friends and family next year.
I began rolling cigars a little over a year ago. I've since rolled a couple of thousand. Each smoke begins as whole leaf. For a small corona, I strip 1 to 1-1/2 leaves. Two to 2-1/2 large filler leaves will make a big honker. Filler can be stripped with less care than the wrapper. I cut the filler to size. I strip a wrapper leaf; mist the wrapper strips. Roll it. Smoke it immediately.
Bob