Awesome, thanks for all the suggestions - now I need all the money to buy all the suggestions! haha
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Hock the wife's jewelry.......Not that I would do that.
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I suggest buying a sampler off those cigar sites..then take time to enjoy them and learn what you like and dislike. Everyone has different taste buds and flavor pallettes so one person's wow cigar could be another's blah cigar.
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Definitely try the Java Maduro. It's the only Java I've had but it was great and very chocolaty.

Also give the Arturo Fuente Hemingway Short Story a shot. I'm new as well and I really enjoyed it. Little 45 minute smoke.

If you like infused stuff then this is a good sampler. One of the first I ordered.
http://www.cigarsinternational.com/p...used%20sampler

and this
http://www.cigar.com/cigars/viewCiga...P-CIGASST104-2
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I think you'd probably enjoy an Oliva G maduro if you're looking to make the move from infused smokes. Seems to fit right into that medium slot for me.
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Man O War Virtue
Oliva G (Natural or Maduro, they're both good)
Romeo y Julieta 1875
Nub (any wrapper is pretty good, these are great to see the differences between the different types of wrapper leaf)
Rocky Patel Vintage 1990 or 1992 (pretty much the only RP cigars I've ever liked)

Any of these are great offerings around about the mild-medium range and can be had for not too much money.
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I picked up a couple Special G's the other day; one Maduro one Cameroon. Excited to try them. Never had an Oliva although I have O and G robustos in the humi and a V that needs to freeze and join the rest.
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Go for a Work of Art Maduro! Very smooth and delicious!
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I enjoy all of them, with the V's being my favorite. I figured the OP would like the G maddies more than the V's as the V's fall more on the Full side of the spectrum.
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I love the Special G. It makes for a great winter smoke and packs a lot of flavor into a little package.
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I haven't really been a fan of any Oliva except for the cains and the nubs.
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Here's a couple of my favorite lighter smokes:

Man O' War Virtue
5 Vegas Classic - Panatella
Ave Maria
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I thought I was a fan of of the milder smokes too, but I am rapidly moving more towards the medium/full body stuff.

That being said, I've enjoyed these milder ones along the way:
Rocky Patel American Market
CAO Gold
Oliva Serie G
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