Well, we know from leakers that there's another Silent Hill game in the works that hasn't been announced yet (so not 'Silent Hill f' or Silent Hill: Townfall').
If I were a betting man, it's either going to be 'Silent Hill remake' (as they'd have to do that before a remake of 3, but if so it won't be Bloober sadly) OR (and it kind of hope this is the case)a Silent Hill classic collection similar to what Konami did with Metal Gear Solid; I think they've learned their lesson from the terrible HD remasters; I'd love a 'Vol 1' that features the original 4 Team Silent games in their PS1/PS2 format to play on modern consoles.
As for Bloober, whilst I'd love to see them do them all, I'm sure they made a comment that they chose Silent Hill 2 as it aligns more with their style and that they didn't care for the 'cult' aspect (so they may not be keen to do Silent Hill 1 and 3 themselves) - but I think Silent Hill 4 would be more "them". :-)
Also, Bloobers new game was just announced for next year (new ip) with a cinematic trailer and snipped of gameplay; 'Cronos: The New Dawn' is a third person survival horror with a cassette futurism style set between a post apocalyptic Eastern European future, whilst travelling back to 1980s Poland to try prevent the calamity; if 'The Medium' was their audition for Silent Hill, then this kind of looks like an audition for Dead Space (but I can see the silent hill influence with the future being the sort of brutal 'otherworld' carnage, and the past being more relaxed) it'll be a day one purchase from me, I love their games :-)