I only use the online.
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Cigar Geeks is def worth the $4 IMO. Use cigar boss for a while. If you find yourself committed to keeping track of inventory, upgrade to cigar geeks. If you find out in a few weeks it's a pain in the ass to update everytime you smoke/buy a cigar, you will be thankful you didn't waste $4
i use little stickers and mark the date i got it and if it was in a pif or trade i mark it as pif or trade as well. after marking it i put it in the humidor and forget about it. im a firm beliver in KISS. i only use stickers because i can see the date better than writing it on the celo with sharpie