I don't suppose many people would count Love's Labor's Lost as their favorite Shakespeare play (though Harold Bloom seems more or less besotted with it, and Harley Granville-Barker thought he saw possibilities in it). The plot is thin enough that you can read a newspaper through it. And the text exhibits a riot of wordplay, the sort of thing that never was Shakespeare's most attractive aspect, and in any event a feature that gains nothing from the passage of time. Yet Shakespeare at his worst is better than almost anybody else at his best, and just about everything he wrote is at least interesting, even if not completely satisfying.
I'm old enough to remember a time when respectable people could say that LLL was so bad that it must be Shakespeare's first play. I don't think many people hold to that view any more. We've got good reason to think that perhaps seven or eight other plays might have been earlier which evidence, if true, means that we are now nearly a quarter of the way into Shakespeare's career. So he is still learning (interesting that Verdi was another sort of late starter--I don't think show people get that kind of leeway very often any more). And even if still learning (but Shakespeare was always still learning), here he is pretty much on the cusp--just beginning to figure what he's got and how he can use it. Bloom again (I repeat from memory)--this is the play where Shakespeare discovers that he can do just about anything with words.*
Apparently we're not sure of an exact date, but the best guesses appear to put it somewhere between 1593 and 1595--so, perhaps coterminous with the sonnets (themselves like LLL, sometimes fussy and over written). Also thus perhaps a bit before Richard II and Romeo and Juliet, both miraculous in the sense tht they are plays in which Shakespeare at once indulges his weakness for overwrought verse, yet at the same time criticizes and ironizes it. Consider: Romeo is a young man who gets some of the best lines, yet fails to grasp that words are not life, and dies for his trouble. So also Richard, a glorious poet but a disastrous king--or rather, a disastrous king because he is a glorious poet.
I'd put LLL in the same bin with those other two, and in the same perspective: the very success of these young people (these young men)with verse betrays a certain schizoid inadequacy at the task of real emotional connection. It's this kind of insight, best appreciated when you think of the play in the context of the larger oeuvre, that makes you realize that Shakespeare even now is always thinking, thinking, and usually one or more steps ahead of you, even when you are enjoying him in your slow-paced way.
A couple more points about context. I always marvel at Shakespeare's capacity for self-correction, his ability never to make the same mistake twice, together with his knack for doing the same thing in a same-only-different way. Both traits are in evidence here: one this is the only play (save Tempest, his valediction) in which Shakespeare did not pillage his plot from elsewhere. You can almost surveying his handiwork and saying, "right, plot is not my strength, better go back to the model of plagiarism-plus-improvement that has served me well before." And two, the play-within-a-play: Shakespeare does one here but it comes across as gratuitous and unkind. He does it again just a little later in Midsummer Night's Dream, where it is tightly integrated and one of the funniesst, most charming bits he ever produced.<
All this is by way of background for understanding this season's Ashland venture at LLL. In short, I'd say Ashland's is about as successful as we have any right to expect. The cast doesn't completely conquer the script, but nobody conquers the script, and they do pretty well with it. Meanwhile, the text is malleable enough to allow for the kind of extras that Ashland does well--costumes, music, miscellaneous horseplay. Indeed oddly, there is perhaps a bit less of extraneous trim here (where the play can take it) than there was in, say, Midsummer Night's Dream (where it was often a distraction).
*Afterthought on dating: I have "my own" theory on dating the play--"my own," in the sense that I thought it up on my own, though I doubt it is original with me. Specifically: we know the theaters were closed through the 1593 season, thanks to plague. We know that this is the time when Shakespeare wrote a good many of the sonnets. We know he emerged in his first glorious flowering about 1595. Some people also speculate--and it sounds right to me--that LLL was written for private performance, not for the public stage. So far so good--but what if he wrote it for private performance during 1593--i.e., at the same time as the sonnets, but unconstrained by the ban on theaters, and unconstrained also by the demands of a public audience. Pure speculation of course, but that is one reason why the study of Shakespeare is so much fun.