I think at it's core, Widening Gyre is an admirable concept. Batman realizes how screwed up his life has been and how miserable his obsession has made him through every meaningful relationship he's had, be it with Silver or Dick Grayson. So when he experiences some genuine happiness that he finds himself capable of intertwining with his mission, he realizes he doesn't have to devote his entire life to sulking in the shadows and can still be an effective crimefighter, while leading a life of his own during the day.
That said, I've found some mischaracterizations in the book to be distracting and jarring, to the point that I can't really enjoy the story for it's strengths. And I don't mean "Oh god Batman peed himself!!11", I mean his mannerisms. Batman sometimes monologues in a way that makes him sound more like a typical New Yorker stereotype than a man of Bruce's eloquence. And then the random elements, like Silver constantly calling him "Deedee" and acting like your general sixteen year old girl, just add to the ludicrousness of something that I'm sure Kevin Smith meant to be taken seriously between the moments of innuendo and DC Universe cameos.
Personally, I loved certain moments in the last issue. Batman taking Silver to the Fortress of Solitude's garden to give her a rare alien flower, then teleporting her to the JLA's moonbase, and his subsequent paranoia shown after [BLACKOUT]he proposes[/BLACKOUT] are genuinely good character moments that display Bruce's amateur nature towards being in a healthy, normal relationship. I even commend the ending twist as something out of left field, a moment that I really didn't see coming in a medium full of cliches - even though I probably should have, given how conveniently [BLACKOUT]Onomatopoeia's storyline was allowed to end in Cacophony.[/BLACKOUT]
I guess my point is, this book has problems that are far worse and far more distracting than this. It wasn't a great moment, or even a dignified scene, but it wasn't the point that should have told people "Uh, WTF?" in regards to Widening Gyre's portrayal of Batman. Even in my praise of the book's good elements, I can't find a single reason to excuse Smith's blatant off-kilter stylings that didn't plague his previous comic book works.