A few random cigar thoughts and suggestions.
You won't ever go wrong with a Rocky Patel Connecticut. If you go to Cigars International, they have a 20 stick sampler with four different styles for $60.00. Sometimes you can get them for less using their "Make Me An Offer" page.
A lot of people go to Canada or the Caribbean and think they are getting Cubans, but are not. There are a lot of fakes out there and the truth is that a good Dominican is so close that only experts can tell the difference.
A few years ago I was gifted a box of Habana Cohiba's. I won't go into the details, but when my friend and I sat down to smoke the first two, we agreed ala "Seinfeld" that they were real and they were spectacular.
Back to cigars. Right now, I mostly Smoke Bobalu Cigars "Tres Capa" three wrapper "barber pole" cigars. They are between $8-10, depending on the size and style, but are well worth it. Hand made in Austin, TX.
Another not very expensive cigar, also from CI, is the Pioneer Valley Especialles. Very reasonably priced and mild. The wrapper is Connecticut shade grown tobacco.
Actually, that last is the best value per stick and I'd recommend it as a good introduction to hand made cigars .