there's an interesting comparison made in playthings on the topic of the home that i keep coming back to. sam and dean are, technically speaking, homeless, and this episode is about a home—a home which, as it turns out, has generations of history behind it. the inn has been in susan's family for over a century. it sits in stark contrast to sam and dean's nomadic lifestyle—sherwin (speaking on behalf of susan and rose) and dean can't connect on these grounds because dean has never really known the stability of a home, and susan and rose have never really known the instability of homelessness.
what i keep thinking about, then, is that sam and dean are paralleled with maggie and rose. these are two characters who are trapped within the confines of their home, swallowed whole by its walls.
maggie can't leave her home, and rose dies to save maggie, willingly trapping herself within it as well. this is a good, happy ending, with both of them finally at peace now that they have each other, alone together forever.
if maggie and rose are trapped within their home, and maggie and rose are sam and dean, then that would imply that sam and dean have a home to be trapped within as well.
i think you can make the argument that the house they're trapped in is their codependent relationship. it's the focus of the season, after all: they're settling into their codependency, learning each other in a new way now that they've accepted this twisted relationship they've chosen. it's the crux of the tension between them as they struggle to understand what codependency means for themselves and each other, misunderstandings popping up left and right because they can't quite get it right. dean is choosing sam, sam is choosing dean, but they're doing it in ways that don't quite match, or ways that have disastrous consequences.
playthings, then, shows a "good" ending for them, a conclusion with hope and promise and ideals. if you consider maggie as sam (the "monster" of the story, the unfortunate child who suffered a fate they had no control over and who simply wants to be loved, to have a family), then dean is rose—the keeper, the one suppressing the monstrosity from affecting those uninvolved until a stroke of weakness allows the monster to leak out, an accident which can only be rectified by self-sacrifice.
in reality, the "monstrosity" is simply a violent loneliness. maggie wants someone to play with, and sam wants to belong inside his family unit. whenever sam isn't accepted into his family, he's pushed instead toward his fate, toward azazel. when dean isn't pulling him closer, he's being pushed toward the monstrosity of destiny. it's a violence of circumstance, a violence brought forth by neglect and ostracization.
the only way to quell the "monster" is through the family. the keeper must die, or rather choose to stay with the "monster" forever. rose dies so that maggie will have a playmate. she placates the spirit and they live happily ever after. it's hopeful, promising. there is a way out of this cycle of tragedy.
just two episodes prior, dean nearly does the same thing. he will die alongside sam so that sam doesn't have to be alone. he will die alongside sam so that he doesn't have to be alone. within the context of croatoan, this was the correct choice that dean made: he abandoned his duty to john and his fate and chose sam above all else. he went against the judgment conditioned into him and followed sam as his moral compass. he embraced whatever monstrosity might spill out of sam and chose it for himself, too, because he couldn't leave sam to suffer alone.
there was a way out of their cycle of tragedy.
the conflict presented in seasons 1 and 2 (and beyond) is that of the winchesters' fates versus their family. as a result, whenever they aren't choosing each other, they're inevitably following the paths to their destinies. playthings therefore shows the "good" end, the way out of that destiny: if they decide to save each other, they will escape their fates as the mythical cain and abel, as michael and lucifer, as hunter and boy king. indeed rose begins the story using hoodoo to bind maggie's spirit, suppressing and rejecting her. they start as opposing forces until they choose love, choose each other, and come together to escape their fates, finally existing on their own terms outside of the story of good and evil.
sam and dean, too, have the ability to transcend their destinies, close the book, and abandon the story. it's exactly what dean tries to do throughout season 2, until azazel forces their hands to move the plot along. while sam is busy fretting about his destiny, dean's head is clear: he's going to save sam, choose sam, destiny be damned. dean goes down the same route as rose. maggie and rose therefore show what could be, what would be if they both abandon the story for each other.
by positing maggie as an allegory for sam, there arises some interesting suggestions about sam's desires and needs. maggie wants someone she can be with forever, without anyone bothering them. someone to play with, to share her every moment with, to be locked in their own little world with for the rest of time. if maggie is sam, then perhaps there is something of these desires within him, as well. sam's violent protectiveness of dean supports this idea, and so does his rather enthusiastic abandonment of society to form a codependent relationship with him—the beginning of season 2 depicts sam as being much more devoted to this codependency than dean is, while dean is struggling with john's death and his new conflict.
maggie's core fear is being alone. this is rather synonymous with sam's core fear of being excluded, and understanding them as parallels develops both of them as characters: sam's isolation mirrors the isolation maggie felt for however many decades rose spent binding her spirit. there's also a fine distinction between sam's core fear and dean's, which is illustrated through this comparison—dean fears abandonment, the people he loves walking away from him. sam on the other hand fears exclusion, which is not exactly the same. exclusion can mean being held at arm's length, knowing that his loved ones are in on something but not himself being part of it. maggie is trapped inside her home; she can't leave. at the same time, her family has grown up around her, and she has watched them become different people without ever being able to interact with them. the binding of her spirit doesn't magically erase her presence from the house; rather, she implies quite directly that she was aware of the time passing when rose was "keeping her away." maggie is an outsider inside the home from which she cannot escape—very much like sam, who is trapped inside his family unable to extricate himself from their confines while simultaneously being isolated from them.
and in this way the pierpont inn—the home—becomes a symbol for the family. the home in playthings transforms from a prison to a sort of freedom and peace when rose chooses to trap herself inside of it alongside her sister. the family is sam's prison, but if he chooses to stay with dean and dean chooses to stay with him, they can trap themselves within its confines and escape the monstrosity lurking outside. and this, the show suggests, is their happy ending, at peace among each other, alone together forever inside the walls of their home.
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