Good for you. I am a long time cigar smoker just taking up the straight edge shaving side of it. As mentioned Anything by Drew Estates is great (espically acid naturals). I am very partial to Rocky Patel vintage 1990's. The advice my brother (who keeps hundreds of high end cigars aging at all times) gave me when I started was. Smoke whatever tastes good to you regardless of price or "image" but also remember that if you are smoking a swisher sweet don't expect to be able to talk to other cigar smokers about its merits because it would be like going to a wine tasting with a $6 box of wine and wanting to be taken searously. With that in mind I usually try and stay above the $10 retail (even though I hate to use price to dictate what a good cigar is you have to get above a certin price point before you get a real cigar) because thats where you get actually quality rolled cigars that are infused with flavor vs flavor cristals added.
With all of this in mind buy sample packs online because if you buy from your local tobacco store: A: their humidors are not always great, I remember one time I was in one and I looked to the back of the humidor and it opened up into their stockroom
and B: you will go broke.
As far as your own humidor cheaphumidors.com is a good fair place with nice stuff. Get yourself a cigar oasis automatic humidifier because it will save you loads of hassle trying to keep the humidity right(i live in arizone and have to fill it 2x a week)
Some good places to get cigars are cigarbid.com (I find great deals there from time to time) and cigar international always has solid prices.
PM me if you have any questions, I am off right now to go sit on my porch and enjoy a frosty mug of A&W and a Guirka Legend (cant remember how to spell Guirka
)