Welcome to the addiction. You are traveling down a road no one looks back on. If you listen to the guys on this board, they will never steer you wrong. Everyone here is knowledgeable and are always willing to help a person just starting out. There is no flaming of newbies on this board, so don't be afraid to ask the simple or dumb questions, just expect some friendly ribbing from time to time.
As for the humidor, the best way I have found to season it it to get a small bowl of distilled water and let it sit in your humidor for about a week or two and let your humidor come up to the right humidity level. The standard is 70% humidity but a lot of people also think that 65% is good as well. Make sure you buy a digital hygrometer, the analog ones just don't cut it. Innacurate reading can lead to you spoiling some good smokes. Then add cigars little by little so that you do not have huge swings in humidity. In the mean time if you have a bunch of cigars, keep them in an airtight tuperware container with a water pillow or boveda pack until your humidor is ready. That should keep them humid enough.
As for cigars, if you like macanudo's, don't buy a buch at once until you have tried a lot of different cigars. I find that a lot of people start out with them but after trying different cigars with more flavor they don't really go back to them. Before I started smoking "real" cigars, the Macanudo Portofino was my favorite.
Now I will not even buy them. If you want to try something new that is not too much, I suggest the Cusano 18 line of cigars. They are for the most part pretty mild, but have a lot of flavor. You can start to work up to the more full bodoed ciagrs and then see what you like. The more you try, the more you will be able to figure out what you like. Good luck on your journey my friend, its a fun one.