Just stumbled upon this and had to get my two cents in. Great starter line is Perdomo Habano Connecticut. It's still one of my go to cigars. One of my favorites wasn't incredibly expensive, but a little higher than an every day cigar. It was a rocky patel decade; very smooth and creamy. Not a blem and very consistent.
Oliva makes some nice cigars too. They also make a line called Nubs which although stocky, aren't so quick like a short story (which is also good). The nubs are pretty neat and I've come to like them.
To be honest, my first was a CAO honey which people will knock, but was a great intro cigar.
I'm going to find a way to smoke this weekend. Sounds nice and the weather should be warm and breezy. Perfect.