I lived in Sydney for a while. The heat is usually worse in Singapore, but at least the ozone layer is thicker.

Expats can still rent HDB. Just can't buy subsidized HDB.

If you have kids here and want to use the local schools, I would suggest getting PR or citizenship perhaps.

I've paid out of pocket for medical expenses recently. Wasn't that bad overall, and all fairly transparent up front. But am back on company provided insurance now. With gold plated insurance, my raw medical costs are sure to go up, since I don't care about keeping them low anymore.