I think this sounds like an interesting evening.
I haven’t smoked a cigar since 1982 when my doctor determined I was allergic to tobacco juice (i would bite off the end of a hand rolled cigar before lighting it).
I come from a long line of cigar smokers, but it ended with me.
My maternal great great Grandfather was brought to this country from Germany in 1868 to run a handmade cigar factory in NY. If you have never seen cigars being rolled/made by hand it is quite an artisanal skill.
I do think there are other more Jewishly appropriate skills that could be highlighted at a Yeshiva fundraiser. I’d love to watch a good calligrapher/sofer craft Ketubot, or a silversmith craft kiddush cups or candle sticks.