A remake of the most popular game in the series is also a great way to reinvigorate interest in the franchise after a long hiatus. Why shouldn't they play it safe before delving into new territory?
Yes and no. The first Silent Hill sold really well in Japan, but the second one did not. The second one however did really well overseas, and this trend continued for every game. In Japan, the series has never been that popular (besides the first game which was a huge hit), so for that reason it makes sense that they remade SH2 first because the Western market is simply their biggest market when it comes to Silent Hill. Of course there is a small but loyal fan base in Japan, but it's nowhere near as big as in North America and Europe.I will have to disagree with one point here. The most popular game in the franchise was in fact the original 'Silent Hill', which sold 2 million copies as opposed to 'Silent Hill 2' which sold 1 million copies. 'Silent Hill 2' is the most beloved by the fans so it speaks volumes that they are remaking a fan favorite rather than trying necro a corpse that outsold it.