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Top Five Cheap go-to's

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Lots of great suggestions so far but one that I haven't seen mentioned is one of my go-to sticks, Joya de Nicaragua Red. They are about $5. They are mild but still have flavor.
 
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Ramon Bueso Genesis (buy and bury for a few years and they're wonderful for those that like em stronger)
Ashton Connecticut Half Corona - a short fill machine made that does everything a connie mild should. Rich creamy sweet nutty flavor. Perfect, if but a bit short...
Joya Red. A newcomer that delivers if you enjoy milds (I do) One of my favorite new releases

ETA: Famous Nicaraguan Selection bundle cigars are excellent after a bit of age. 8-10 months and they start to shine.

HUHC and Party Short are pretty much my go-to 75% of the time, and they're relatively cheap around $5/ea
 
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ChipS

Chip
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I only keep 3 of these in the humidor these days but is a decent mix to start someone new IMO.
Genesis (I prefer Habano)
MUWAT baitfish
Onyx Reserve - little too sweet for me now but was fantastic when I started
RP Connecticut - very mild
Nica Rustica
 
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