Sorry - don't drink so I can't really be any help with pairings.
But I don't know that you have to go so high end on the cigars. It's a charity thing and maybe there will be someone there that knows about cigars, but most likely it will be a wife trying to get them for her husband or someone just looking to donate. Padron, Davidoff, My Father and Fuente are big names that the weekend smoker will recognize - I'd stick with those type of names. Cohiba, Ashton, Camacho, Montecristo, Macanudo.

Really nice gesture by your wife to make you do this Dustin.