No clue if anyone here is an avid Cigar smoker, however, I am a newbie at it, and am enjoying the experience thoroughly, and am wondering on your favorite brands, and a choice humidor. (I live in America so no Cubans, sadly)
^ Smoking is a terrible economic decision. Huge money pit. If you're trying to make this some " mellow on-the-side " thing, then stop while still you can. I honestly thought this would be about how smoking is bad for you in 50,000,000 different ways, not advice on how to smoke better. smh
Ignore the "quit while youre ahead" crap and go buy the good stuff. If you can control it, smoke if you want. I know I can control my addictions (smoking, drinking, gambling), so I can do so relaxed. All it takes is self control.
You can know, but only you. If you don't feel safe with something then maybe you are at risk for self control issues, but there are plenty of people (albeit a small amount) who smoke or drink on the side, or socially, and not addictively.
Cigars heavily depend on your personal taste. If you're just starting out don't smoke the likes of Partagas or Cohibas since they'll just leave a very bad taste if you can't withstand the strength. For a first time I recommend Romeo&Juliet, great light taste and decent smell. My personal favourite when it comes to middle-strength are Monte Cristo, very classic, they agree with almost anyone. If you really want something stronger, artagas might be your best choice. For example Partagas are usually much cheaper than Cohibas, but far better in terms of taste. Generally I recommend looking out for overpriced cigars like Cohibas (note that my experience is from Poland, price differences might be smaller in US), also in the meantime start trying out random middle-shelf cigars, like Don Tomas, maybe something from Nicaragua, or whatever is available nearby. Also I heavily recommend starting by shopping in a specialised store rather than online, since very often people running the shop will be able to give you a lot of good advice. Only later go into internet since it'll reduce your costs if you take it up on a regular basis.
p.s. If you are starting, don't even think about a humidor, better try out 1-2 at a time at parties and develope a taste before going all-out on buying cigars.