I think you're going to get a lot of advice in this thread, mostly from guys who will be somewhat knowledgeable and who will give you some solid guidance.
Here's my counterpoint to the people who will suggest you buy this and buy that:
If someone were just getting into pistols and he asked you what kind to buy and what equipment he'll need, wouldn't you first suggest he go to a range with an experienced friend and try out the hobby, shoot a number of pistols, before he made any investment? IMHO, this is the same. Go out to a cigar night with some CR guys, try different cigars, listen to their opinions about humidors/humidifier media/lighting techniques. Find out what you like and don't, what you're willing to invest in vs. what you consider a waste. THEN start spending money. Your tastes will change somewhat as you get into cigars more, but if you start with some good basics, you'll enjoy it more and will get to what you like a lot faster.
My 2 cents.