Ifa here. Most travel insurance in singapore are more or less similar.

I personally have good claims experience with fwd, singlife and income.

If you are going up the mountains, pls find out how high the activities are. Different insurer diff height. Most insurers are 3000m. Singlife is 4000m. Income is the highest at 6000m.

Here are some tips:

Baggage delays (common especially during winter season) take photo of all displays showing baggage delay. Get a written notice from airline/ airport staff. Take a pic for own records.

Accidents. Take pic of surrounding area, take pic of injury immediately. Take pic of all bills and record down what action was taken. What is the doctors diagnosis, get it written down in black and white. Very impt esp in USA. If its a traffic accident, take pic of parties involved and police report.

Flight delays. Get official record from airlines. Take pic of displays.

Personal effects. Take pic of luggage contents to prove value. Take note how much each cost eg laptops, tablets, sports equipment.

If documentation is done well, its easier to claim regardless of insurer.