"But the other roaster has my favorite Santos all year long."

SEASONALITY
"But the other roaster has my favorite Santos all year long." ... First things first, Santos isn't a producer, but the port in Brazil where a lot of coffee is mixed and sold as Santos grade. And that might be a good point where to start with freshness and seasonality, as it is linked to transparency. In mixed coffees of the C Market grade, you can't tell what's fresh and what is not, as it's all mixed together and it's almost untraceable.
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To put it simply, one can't make old green coffee taste great. If you're a specialty coffee roaster, you can rehydrate, soak for longer time when roasting or barrel age the coffee to give it something extra. That's all good, but it's not a fix as much as it's a makeup. That's why it's always important to buy fresh crop green coffee for better cup quality, buy smaller quantities and roasting them within 4 months ideally. 
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FRESHNESS
"Why don't you buy more bags if you want to support the producer?"
We have a rule that new coffee shouldn't be offered longer than 4 months in a row (as long as we don't have an AC controlled storage room for greens). The freshness is related to moisture content in green coffee. In terms of the sensory experience, older green coffee loses acidity and aromatic atributes first. That can start happening the 6th month from harvest, more often after 9 months and sometimes after 12 months (dense coffees from high alt). To illustrate that on an example: I had 2 pour-overs from our Peru in October. One bag was roasted 10 days ago, the other one 2.5 months ago. The older bag tasted better, as the green coffee was fresher when it was roasted. Lively acidity of yellow stone fruit was present, more sweetness - the coffee had better overal character. The freshly roasted bag didn't have that, although the roast data were the same. It was heavier on body, a little bit dry in finish, acidity was toned down.
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Sometimes, but that happens only to the best coffees, the coffee is stored in parchment and in bags before dry milling, parchment being a great container for preserving moisture. It can be stored like that even for 6 before shipping. I always observed that I have a window of opportunity to sell the coffee in it's freshest state until 10 months from harvest until acidity started to decline and fade out and a slightly papery/harsh sensation started to build it's nest at the bottom of each cupping bowl and cup.
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Buying fresh green, roasting fresh green. The outcome is tastier and makes a better representation of producer's hard work.