Yeah, and who's to say Robbie the Rabbit didn't just expand beyond SH anyway? Eileen had a stuffed Robbie doll in her room, and she was in Ashfield or whatever that place was called. That's not to say that she didn't just go there one day and bring it back, but still.
It's just an easter egg plain and simple. But if you really want a storyline answer then just because Josh has one doesn't mean he went to Silent Hill. For all we know his dad Adam could have went to Silent Hill for whatever reason, picked one up, and brought it home for Josh.
I love the Silent Hill Series. The new games did nothing wrong whatsoever, they were developed well, and did things different. I believe that Silent Hill Downpour will make all Silent Hill fans happy. Team Silent doesn't exist, but their series does.
Sorry to post in a thread that hasn't had activity in a few days, but I really laughed at this. Hard. This is over analyzing at it's best. Who cares why they had a Robbie doll, it was a reference. This reminds me of the whole "everything has to be a symbol" people