Find yourself a good local shop and use it.

Tell them what you've tried and liked (or start with some of the above-mentioned brands) and ask for a few suggestions you might like.

I personally suggest buying as many single sticks as you can right now and not going for deals on boxes. Your tastes are likely to change the first few months you start smoking good cigars, so you don't want to get stuck with half a box of something you don't like.

I find walking in to a shop with a list is tough. You never know what any given shop will have at any given time.

Don't be afraid to ask for suggestions. I don't think it makes you look like a noob, I think it makes you look like someone looking to expand horizons. Noobs buy whatever was in the last issue of CA