Maybe too much info but since you asked...
I'm highly OCD so do / keep:
Spreadsheet of all the cigars I've bought or received. Has info on the cigar itself (...color, origin, wrapper, binder, filler, shape, strength and size...), where / whom I bought / received it from and price. Also cells for date(s) of when I smoked / gifted them and comments.
Tag each cigar with info which may include vitola, who sent it, when I received it, box code, etc.
Cigar calendar - tape my bands onto the date I smoked a cigar
Recently started another spreadsheet in which I track what cigars I smoked and when. Different than the calendar in that it's keep in alpha order so I can see how many of each brand and vitola I've smoked at a quick glance rather than flipping through each month counting how many R44s / PCRs, etc. I've had this year.
Used to, when I had much less cigars and storage containers, track where every cigar was (...told you I'm highly OCD...).
I pretty much blame my OCDness on my Dad who was a finishing carpenter. He would date every box of nails, screws, etc. and had a first in, first out rule. He knew where everything was, often times he would have me return something to his workshop and tell me the exact location - Center shelf, 4th row, 3rd one from the left - while he was in the house. Of course he was always right.
Okay, that's it.