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If your visa expires on May 17, and if you leave the country by May 18, it's still a one day overstay. There will be a fine to pay, but the worst thing is you will be registered as you overstayed. And trust me you don't want to do that.
Going to Malaysia from Singapore is one of the easiest overland border crossings.
You can easily take a bus from Singapore to Kuala Lampur.
If I were you, I would go to the woodlands by May 17, get my passport sealed, and go to Kuala Lampur by train. Woodlands is the Singapore side of the border, and Johor is the Malaysia side of the border. You can easily take a train to go to Kuala Lampur (takes about 5-7 hours).
You can also try to extend your visa. Since you have two weeks to do that, do it from the the Singapore embassy in India (Delhi one is quite friendly I heard).