i understand the challenge here but what you're looking at is relatively lower tier bourbon and cheap-ish cigars if you go down this route. Not saying expensive (and that's relative isn't it?) is necessarily better.

So to meet your challenge i would recommend Elijah Craig Small Batch (which comes in around $27) and for the cigars something like LFD Chiselito Maduro which are a decent smoke and combine to make mission here.

https://www.cigar.com/...duro-cigars/1513365/

Upping the ante to around $100USD total and a much better pairing i would recommend would be the LFD line on chisel tip cigars but in the Habana Maduro Gordo along with a bottle of artisan dark rum from Richland Rum in GA--this stuff is just flat out great!

http://www.richlandrum.com/

hopefully this is of some help--a noble quest Amigo!

/r

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Steve