My Bostons weren't super comfy right out of the box, but they broke in super quickly and are now the most comfy footwear I own now. I've worn them on several spontaneous hikes and have had no issues even with rough/steeper terrain.
How many days are you here for? Think there are a fair few Singaporeans on both swd and cm.Most of the good food are in central/east side. It's been raining pretty much every day this week (monsoon season) so keep that in mind when packing.