The question I have is: Should I buy a box of one line of cigars or spend a little bit more and buy several individuals so that I an afforded some variety?

I know this is a matter of opinion and will bring forth troops for both encampments, but I would appreciate the views of the rest of you very much.
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How new are you to cigars? If fairly new...I would recommend that you try a variety of sticks. Once you have found something that you really enjoy...then snag a box.
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I only use a 100-150 count desktop, and while I have bought boxes, I tend to buy fivers mostly.
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that's totally an issue of personal preference. i find that variety is certainly more appealing. there are a plethora of samplers available out there.
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How much storage room do you have? Are we talking a 50 count desktop humi, 300 count footlocker, or something significantly larger? If it's not a lot of storage real estate, buy some singles and/or 5'ers. Get some new sticks in singles to try 'em out, get some 5'ers of ones you know you like. If you have more room and the money to do it, stock it with a box of cigars you know you like and then a few 5'ers of new cigars to try.
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If you have a certain brand you like, i.e Tats, DPG, Oliva whatever, buy a few samplers from the brand you like, find the sticks you enjoy from the brand then get some boxes down the road :-)
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Personally I am one for diverstity, I like to grab 5 packs or even pairs. Sure if there is a good deal on a cigar I KNOW I really like I'll splurge on the box, but personally that is few and far between. What smokes are you thinking about getting?
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I should have clarified that. D'oh.

It's a 40 count desktop, so my conundrum is that if I buy a box, I'd be only smoking from that box until I run out again...

Although I'm seriously considering making a cedar lined Igloodor...

When I got hooked, I got hooked hard.
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I hadn't thought of that, actually. For some reason that third option never popped up.
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Stick with singles, there's no reason right now for you to commit to anything more than a 5'er (and even then maybe avoid that for a little while).

When I was limited to a 50 count one of the biggest mistakes I made was dedicating half of my humidor to a bundle purchase I made. Great sticks, but it really limited my cigar selection. While I should've been trying new things, I instead was mostly smoking that one cigar.

Once you find some favorite sticks and have the money, upgrade the storage and buy 5'ers. Even then I'd avoid buying full boxes (unless you go through a lot of cigars). Personally, my tastes changed so much within the 6 months of really getting into the hobby (this was after 5 years of casual smoking) that I was left with boxes of cigars I loved just a few months back that I no longer cared for.
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If you are asking the question, I assume that you are still quite interested in exploring different sticks as opposed to just having a couple of brands on hand all the time that you really like. Therefore, buy fivers at some place like The Devil Site . The price won't be much different than boxes and you can gradually settle on a couple or three "go to" sticks that you want to have on hand all the time.
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That's a very good point. That's what makes the most sense and it seems to be the general consensus, so my mind is made up.
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I started with samplers.(full of singles or 2's) that way I could cover as much ground as possible. then 5 packs when I found something I liked now I'm getting a box or two here and there and "super samplers" (like 20-40 sticks of many 5'ers). If you just get one whole box at time, man it will take years to start finding what you truly love.
:-)
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Why is CBid so dubbed, anyway? Hah
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Wait til you get on and start bidding, you will know why :-)
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Ohhh. I thought it was something that they had a bad reputation for.

A bad reputation for something other than pushing B/SOTL in to poverty.
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Nope, that's why :-)
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I don't know if I'll ever buy a box. Fivers and samplers for me. I'm still new though.
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I started by getting samplers so I could try lots of different sticks. Now I do mostly 5 and 10 packs of the ones I like. If I really, really like something I'll spring for a box.
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It cases Divorces annually.

I'm not sure where Grand Blanc is, but I'm from Newaygo (About 30 Miles North of Grand Rapids.) Glad to see another Michigander on here! Welcome to the Forum.

I also agree with getting 5'ers, instead of a box.
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