Cigarbid is the place I get the best deals. Bid on many auctions at low ball prices to do the best, don't fret when you lose an auction because the item will turn up again in 2-3 days again tops.
Cigar International runs cigarbid, always check the price of the cigar there before bidding on it. Ocassionally the cigar is not also availbe on CI, but it usually is. Often you will see overcompetitive bidders paying more on cigarbid auctions than the Cigar International price. When setting up your
Cigar Bid account, be sure to choose weekly shipping option to save a bundle on shipping charges. All of your "wins" in a week are combined into a single shipment and you only pay full shipping price on the highest item; each additional item is usually $0.50 or $1.00.
Other Online retailers that have good prices on various smokes:
Thompson Cigar
JR Cigars
Phat Ash Cigars
White Ash Cigars
My beginner cigar reccomendations are also the cigars that frequent cigar smokers enjoy on a daily basis. The cigars that are good yet cheap.
Here are a few I can I highly recommend: these are seconds/overruns of very good smokes. They may have blemishes on the wrapper leaf and won't have the fancy band/packaging but otherwise have the same tobacco inside; they are highly enjoyable smokes:
Consuegra (AKA "Connie") - seconds from the manufacturers of Hoyo de Monterrey, Punch, Belinda and El Rey Del Mundo $25-$35 per bundle of 25.
Roly - Puros Indios seconds $15 - $35 in bundles of 20 or 25
OLD FASHIONED - Macanudo and Partagas Seconds - $20 - $40 in bundles of 20.
El Credito - seconds of La Gloria Cubana, I haven't done these myself yet, but on another forum a reviewer liked one soo much he used a corn dog stick he found in his truck as a makeshift roach clip so he could smoke it down to nothing! These are sold by size "grouping" so when you buy them you get SM, Med, Lg, XL general sizing.
Flor de Oliva - Olivia seconds that I am going to have to try as many raves I have read about them.
You could also look into "sandwich" or "mixed filler" cigars. These also use the same tobacco as their more expensive siblings, but use a mixture of the clippings from the full sized leaves as filler instead of "long filler". I have had some excellent short filler cigars. Cigar snobs will turn their nose at them, but there are some sandwiches that are even out of my normal price range (Drew Estate La Perla Habana - $5/stick, but look for them on auction and you can sometimes get 'em for $2/stick)
If you want a decent box cigar that sells everywhere at an affordable price you might want to try La Finca in the corona size. I generally smoke larger ring and longer cigars, but the corona really shines in this brand. At one time before the boom I got them at $23/box. During the boom they skyrocketed to $80/box after a favorable review in CA's buying guide issue. They can now be had for around $30/box.
For your cigar storage build yourself a humidor from an Ice Chest. Search cigar forums or the web for Coolerdor, Coolador, Koolerdor, Koolador, Igloodor and the similar. The one I am using now was made with an Igloo 48 qt "Ice Cube" cooler ($12.88 @ WalMart), a $19.99 Radio Shack digital hygrometer, and 1/2 pound of Climaxx Premier Media beads (65% variety) in a nylon stocking. ($23/lb for the Climaxx beads, stocking stolen from wife). The cooler is holding 200 cigars right now at a rock steady 67%, and has room for at least another 200-400 cigars depending on the size. Some people will line theirs with spanish cedar and construct fancy shelves and/or drawers in theirs; I just stack the boxes and put 5 packs and samplers into old empty boxes. You can house 1000's of cigars this way and protect them very well for little investment. If you want then you can also buy any old 10-25 capacity humidor with a super fancy finish for the ones you are going to smoke near term; I keep my soon-to-smokes in a floating tray at the top of the cooler that came with it.
By the way, this is my first post here; hopefully it helps.
Matt