Been there for six years. I'm finally very comfortable bidding there now. It is a particularly dangerous place for a cigar noob who has had little mentoring. There is a TON of cheap cigars available. I know. I tried every one of them. To me, the holy grail was the sub $3 cigar that I enjoy. I sampled literally hundreds of different cheap cigars - many under $2. More than 99% of them, I will never try again. They are marketing masters who write good ad copy and can make any cigar sound mouth-watering, not to mention great 'manipulation' of 'ratings' and 'msrp'.
I'm very glad for the 4 or 5 really cheap cigars that I still buy - for fishing or yard work, etc. But was it worth it? I don't know....maybe I am in a better position to appreciate good cigars now....someone here once said you gotta smoke the crap to appreciate the good---- probably no truth to that except that it makes us crap-smokers feel better.
Nowadays, I am very selective. For example, I like Tats. But, deals on brown and black labels are few and far between. On the other hand, I won a box of ('relatively' unknown) Fausto FT166 yesterday for $94. You'll never see a deal on an LP, Opus or Anejo, but the occasional AF SG will slip to you for less than you can get anywhere else. Where you'll often find the most value is in the merchandise, Quickies (only on auction for less than 24hr), and 'mid-range' stuff like Pepin, AJ Fernandez, etc.