Hi Segbert,
Yep, I hail from sunny Singapore

Saw in your post that you're thinking of moving here for your retirement and I'll definitely welcome another DV addict here!
Generally, food here is inexpensive. There are countless food courts, hawker centers etc around the island and if you're not picky, can enjoy a meal for less than SGD10. Main killer expenses here is the cost of property and cars. Property in particular, had been on an extreme upward rise. Just to give you am idea - In 2011 May, I bought a condo for investment in the Central Core Region. It's a paltry 40sqm and it costs close to SGD900k!
Public transportation infrastructure is generally good but it's starting to be overcrowded. Cars (say a Toyota 1.6L) will now set you back close to SGD80-100k which again is extreme crazy.
Live in help (generally domestic helpers from Indonesia, Philippines and Myanmar) is around SGD450 per month. Factoring in their expenses, insurance, food etc, it'll cost you roughly SGD600 per month.
If there's anymore you want to find out, let me know ya