Welcome to the boards HP.
First off, no you don't mix machine made with hand rolled because you don't want to buy machine made cigars, they're crap.
Secondly, you're not going to buy a humidor, you're going to buy a cooler, 60qts. and up. Then, you're going to buy humidity beads from this website heartfeltindustries and get the 1 lb. bag.
Thirdly, cigars are a product similar to wine in that you don't have to worry about freshness, age is a wonderful thing for a tobacco, what you have to worry about is whether the cigars purchased have been properly maintained at a good temperature and humidity level. Almost all cigars purchased on-line come from vendors who maintain their stocks well.
Finally, as for the customs charge, I don't know, Roham and some of the other guys are fellow Hosiers, so they'd be able to tell you more.
"If you look for truth, you may find comfort in the end; if you look for comfort you will not get either comfort or truth only soft soap and wishful thinking to begin, and in the end, despair." -C.S. Lewis, Mere Christianity
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