score:6
Based on your profile, I am guessing you are a US citizen. You get a 90 day Visit Pass when you enter Singapore and you can apply to extend it for another 90 days (S$40 extension fee plus S$30 visa fee as you would exceed your 90 day visa free period - http://www.ica.gov.sg/page.aspx?pageid=180&secid=178).
But as a tourist you are not covered under Singapore's health coverage, as that is for citizens and expats with resident status. On the bright side, medical costs in Singapore are lower than back in the states and the level of care quite good.
Upvote:1
In addition I'd like to point people to the following link: Visa Policy of Singapore
Western countries appear to be VISA free currently with either 30 or 90 day Visa's. If you want to save some money, you can simply travel to Malaysia by bus and returned to get another 30 (or 90?) days. I've done this several times although it might be best to stay a few days in the other country, I've returned on the same day before.
To travel to JB by bus the easiest way is to take the MRT to Woodlands terminal. Then take bus number 950 to JB. Don't forget to bring your passport. You can hop on the same bus number to return.