I, personally, would rather have mine crunchy dry, but in high humidity Alabama, the longer I leave a tobacco out, the more moisture it absorbs. So, I rarely can get a tobacco that dry without using something like a coffee mug warmer or leaving it open on my dashboard on a very hot day. Usually, when I open a tin or jar, I just dry the whole thing at once to save time having to wait on bowl fulls at a time to dry.
And, sometimes, like when I buy a pound or so of Habana Daydream or PS Cube Cut, I just leave it in the bag and leave the bag open. I may put a day's worth in a jar to carry with me, but when I have no interest at all in aging, why bother?
I don't smoke a lot of aromatics, but when I do, I don't bother drying them at all. The taste or aroma for those comes from the toppings, so I don't want to push the flavor off. But, this may factor in to why I don't smoke aros much.
Mostly, I only jar up what I am wanting to age. Whatever I want to just smoke from, I just leave it setting around, trying to dry it out.
I have only ever seen stale tobacco from well aged blends. I'm sure it's possible to dry one till it is stale. I just haven't ever seen or experienced it, ever.