Robby,
My advice would be for a group of five-packs. You can bring back $100 worth if you enter on a legal license/visa. If sweet talked, the worker at the shop can write a receipt for $100 or less, even if you spend over. Max of 50 cigars, though.
Ditto the Siglo series. I dig the IVs myself. Trinidad Fundadores go in 5packs, and you can get RyJ Churchills en Tubo in three packs. Montecristo #3s are winners as well.
My point, you can get a range of 3/5packs and bring back a whole lot of different smokes. For example, the Trinidads go for around $38 per fivepack. Unreal. My feeling is to take advantage of the cheap prices and diversify your portfolio, so to speak.
Just my thoughts. You can't go wrong with any Cubans from Cuba. They are in primo condition due to no shipping/reconditioning effects.
I miss that place already. Thanks for the memory lane jaunt.
John
PS: Casa del Tobaco in La Habana Vieja has better prices than the hotel shops. My 2cents on that. And be sure to provide sealable plastic bags to prevent airport dry-out!