multiple passes are common. There is usually more than enough interest to support running several.
It is not uncommon for a person to ask for help in establishing the initial cigars(especially noobs). I supplied al'Thor on his first and Chip helped me out with rare cigars on mine. I think it is better if they are all yours.
You can also add a twist. Include your favorite beer, wine, coffee, or personal item for the next member in line. Include a gift smoke for all participants.
The host decides who he wants in. I take 1 noob per year when I run one. I can't send $800+ worth of smokes to folks without knowing them.
Check out Homie's he is an experienced host.
