A local smoke shop.

Any decent shop should be able to pick out a "sampler" of cigars to meet your requirements. When I went, I asked for 5 sticks around 5 bucks each. She picked out 5 sticks in the mild to low medium range... From there, I started to figure out what I liked...

People that work/own cigar shops know a lot about cigars (if they don't, go elsewhere)... They're a great resource for finding smokes you'll enjoy