Should I buy travel insurance for personal trip if my company already bought an annual travel insurance for me?

Company bought travel insurance is most likely to cover for biz trip only and coverage may be limited. I'll usually buy single trip travel insurance for my own personal trip, in fact, I'll purchase own travel insurance for biz trip at times, depending on the location and duration. Nowadays we can often get discounted rates due to competition and promotion for travel insurance which is much more affordable. You can go to https://www.gobear.com/sg to compare the various travel insurance plan and rates.

If company buys for you, and Used your name it’s not required to buy. If use company name, you might not get much back. However, some single trip personal travel insurance are affordable (because of competitive market) so I would just add on.

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Unless the work you take part in overseas is high risk (i.e diving, military).

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$100 for much much more coverage is not too much. Think of the persons receiving the payouts if unfortunate events do unfortunately occur.