I think I probably count as a serious wine drinker.
There are as many theories on pairings as there are wine/cigar combos.
My rule of thumb (there are those who go completely opposite) big, bold reds (especially ones that have been heavily oaked or are young and full of tannin) do something with a broadleaf wrapper.
Softer, fruiter reds, go a little lighter on the cigar, but still something with a lot of flavor and medum/full to completely full bodied.
Dry whites, grab something with a San Andreas wrapper, or, like a JD Howard with that Brazilian wrapper that will give you a very contrasting flavor.
Semi-sweet or fruity whites (like a petite manseng) go for something like a Tat brown label or an El Truinfadors that will bring out the fruit notes without muting them
Sweet wines--unless you're doing a port or a mederia, stay away from that stuff. It's gimmicky.