this is actually super complicated to answer. contrary to popular opinion, fresh is not best, certainly not for espresso.
when you roast coffee, the cherries literally pop like popcorn, and they start releasing carbon dioxide. freshly roasted coffee will still be actively releasing co2, and when extracted under pressure, that co2 will become carbonic acid, and the espresso will taste gross. depending on the level of roast, espresso can take anywhere from 3 til 10 days after the roast to "peak" (finish degassing) and then it gradually declines. most espresso is best between 7 and 14 days off of the roast, but that's flexible too - i've had shots from 25+ day old coffee that was mindblowingly good.
if you have ultra fresh beans and you grind them and then let them sit, you can actually speed up this process. for example - i'm a home coffee roaster, and i usually roast on sundays. so if i roast on a sunday, and i want to know how a particular coffee is going to taste as espresso in 5-8 days or whatever, i'll grind the fresh-roasted coffee the night before, let it sit out/degas, and then pull it as a shot in the morning. if i ground the same coffee right before pulling the shot, it would be terrible, but if i let it sit out to speed up the degassing process, it'll be much better. so, if you know what you're doing, option #1 is a great call.
buying nice coffee is always going to be better than grocery story, cheap/shitty coffee, no matter how old it is. speciality grade coffee will peak in flavor and freshness sometime in the 7-14 day range, and during the gradual decline, all of the flavors average together to basic stone fruits, honey/caramel sweetness, or nutty/chocolate flavors (this of course depending on whatever the bean tasted like to begin with - those three flavors are the most "stable" and they last the longest - other flavors, like florals/berry/bright citrus typically fade after 14 days or so after roast).
the other thing with nice coffee is that any self-respecting roaster won't go too far beyond a dark medium roast; any more than that and everything tastes the same anyway - like ass - so there's no sense in doing it. shitty grocery store coffee is typically done to a vienna or light french roast (dark af), which is awful and tastes awful no matter how fresh it is - these roasts are designed to make coffee from different origins taste exactly the same no matter what (so they can switch up their supplier and save 3 cents/pound on commodity grade coffee), and it also hides defects in their green by roasting the ever living hell out of them.
the only caveat that i have is that coffee that SOUNDS fancy isn't necessarily fancy or good - just being local and fresh doesn't mean that the coffee is worth shit, even if they tell you the name of the fucking farm it came from. all coffee came from a farm, knowing the name of it doesn't tell you shit as to whether the farm is good or bad or average. "La Hacienda Esmerelda" sounds a lot like "Hacienda La Minita", but
one of those is an ultra-premium, $90/10 oz bag coffee, and the other is just average.
thanks for coming to my ted talk.
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