Assuming that the money comes from a windfall ie that I'm unaccustomed to great riches (-which is the case), I think there is a tipping (no pun) point where a posh hotel becomes uncomfortable for me - the people who work in these grand places can smell new money and although they will always be very professional, they are probably more snobbish than some of the guests.
It was a life-lesson for me to observe the concierge at work at his counter in one of the top hotels in Vienna, he was very selective in who he would respond to first - it wasn't first come, first served but his eyes would first alight on those he felt it was preferential to serve first.
But given the choice, I think I would go for nostalgia - The Fullerton in Singapore as it's a landmark building and I remember buying stamps there when it was a post office.
I'd give the Raffles a miss as it's a rebuild and like the renovated E&O in Penang, little like the original. But as with most things, if you like it, go for it!