I think it has to do with Alex's mom, he's asking her about why she was left, who left her there etc, she's in pretty much the same situation as his mother, sitting around all day every day waiting for something to happen and he relates because of that, he just finds it harder to actually voice those feelings to his own mother, not that he'd get through to her if he did...
I dont think those memories could be his, cause we learn later on that Alex never went to Silent Hill. Him and Elle both say that they were forbidden to go Silent Hill by their parents. So I'm sticking with the Carol theory. She's more likely as she would fit in the with notes. I cant really see why else those notes would be there.
Oh don't get me wrong, I never doubted that she was Carol, why else would all the notes be in the hotel, they don't reveal anything about the main story whatsoever...I was just trying to explain what I think the significance of her appearance in the game is, acting as a counterpart to the scene in the confession booth...
I really believe that the woman in the hotel is Lilian, not only because of her voice that is the same or at least very similar, but also because of the stuff she asks Alex to get and what she says. Some time ago I've written a theory in my blog:
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.
I haven't played this in awhile, but i'm going with the Carol theory as well...the notes you find regarding her affair and such points to her being this mysterious woman...i don't see her being Lilliain at all.
If this is supposed to be Lilian, explain how she's supposed to be Lilian other than "Hey, her voice sounds similar."
I'd personally consider her to be Joey Bartlett's mother. Talking about how important family is (similar to Judge Holloway's supervillain speech), memories of Lakeside Amusement Park (home of Robbie the Rabbit and merchandise), and an affair with Mayor Bartlett all sort of leads me to believe that she could very well be Joey's mother. After all, Josh and Alex were never allowed to go to Silent Hill. Maybe the Bartletts went there. Perhaps Joey gave Josh a souvenir from the park. Y'know... That Robbie doll he has even though he was never allowed to go to Silent Hill.
Or maybe Robbie is just an international phenomenon in that world. Who knows.
Well, obviously mayor Bartlett frequented Silent Hill, I would assume he didn't take his wife with him while he was banging Carol, though...so why would Joey's mother be hanging around the place her husband had an affair while he's out yelling at grapes and digging up graves [Adventure Time-rhyme, yo! <- And another...brother!]...? It's not like Sam and Carol ran off and are living the good life, leaving the Bartlett wife behind, Bartlett is walking around being crazy.
So IMO Sam Bartlett simply stopped visiting Carol after the ritual failed, too caught up in his personal drama, so he basically forgot she was there and it isn't until Alex comes into contact with Bartlett and Joey's watch that Bartlett is transported back there. I assume it's supposed to imply that that's where he killed Joey, which does seem a bit odd.