I smoke like... 15-20 cigars over the summer months every year, just casually relaxing with friends on the patio or whatnot. My experience with buying cigars online in samplers and bundles and stuff, trying to find "good deals" but without being cheap about it, is this:
Cigars are tricky. Within most any brand there's such a huge variety of cigars, and even the same cigar can be significantly different to smoke depending on the shape (so like, churchill compared to some goofy figurado) and how it has been stored, whether you mangled it trying to punch/cut it, what you're eating/drinking before/during the cigar, etc. I've smoked cigars that get rave reviews online and thought they were pretty meh, and I've smoked $2.00 cigars that were great... but then smoked one of the same $2.00 cigars from the same box stored the same way in my humidor a week later and put it out when it was only 1/3 done.
Personally I just like to smoke them like I would order a sample flight of beers at a taproom: order a handful of stuff I've never tried before but that sounds decent enough based on what I've had before and then try to enjoy smoking them, comparing them to what I've smoked in the past. I'm to the point now where I'd rather pay a lot more per cigar and try some singles from a local shop than get a good bundle/sampler deal online only to realize I don't like 4 of the 6 types of cigars in the sampler and spend a year trying to give those away to buddies.
/shrug
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