One thing I wonder about though is eligibility for DII for foreigners.
The DII issuing carriers in Singapore will issue policies to foreigners. That includes EP holders and DP holders working with Letters of Consent (LOCs). (Yes, your spouse holding a DP can take out a DII policy if your spouse has employment income. "Don't forget your spouse.") So there shouldn't be any access problem as such.
Would it be useful for me (not a PR, both me and wife are foreigners on EP/DP)? Or would I have to leave Singapore “anyways” once I can no longer work. Would a DII still pay for me when unable to work and no longer living here?
All the local DII carriers will eventually drop you once you leave (or are forced to leave) Singapore. As you probably know, if your employer very suddenly fires you, you have to leave Singapore within 30 days. That possible quick march out of Singapore is an overarching problem, and one side effect is that it can make insuring against disability less than ideal.
Most of the policies tolerate
some unemployment and
some time outside Singapore, and Great Eastern's DII seems to be the most tolerant. Really you just have to get copies of the policy letters and read them critically, considering "What if?" scenarios involving departure from Singapore and other scenarios. In particular, would you still have some reasonable coverage time after departure, so you can get covered elsewhere? Would benefits still be paid if you become disabled in that time window after departure? How are benefits paid? (Probably into a bank account in Singapore, so keep one open. Could you spend those benefits in a low cost way from outside Singapore?) If there are medical exams to verify and re-verify disability, how would that work outside Singapore? Who would pay for those exams, and who can conduct them? (Would you have to fly to Singapore for periodic assessments?!?!)
Here are some other things to think about, in no particular order:
1. If you're eligible to upgrade to a Personalised Employment Pass (PEP), consider doing that at some point, particularly if you start to get signals that your employer may want to drop you in the months ahead. If you're approved for a PEP it's a 3 year "ticket," and it tolerates bouts of unemployment in Singapore of up to 6 months (up from 30 days), at least giving you more time to relocate more gracefully -- for children to finish up a school term, for example. You can only get one PEP per lifetime, though.
2. I've mentioned before that it's possible to buy "offshore" DII. I've decided a non-local DII policy is best for me, although I can't say it's ideal. Most of the "offshore" DII policies are "European style," which is to say they pay disability benefits for up to 10 years then a lump sum if you're still disabled -- and that's that. I think I'd prefer straight monthly benefits to age 65, but I can live with "European style." One possible advantage with the non-local DII policy is that it's global, or at least nearly so. The more global aspect of the policy isn't just for EP and DP holders. It's for PRs and citizens, too, who value that feature. For example, if you're a citizen who might spend 5 years working in Silicon Valley at some point in your career, the local DII carriers are probably going to struggle with that.
3. It's also sometimes possible to continue social insurance coverage (which tends to have a stricter definition of disability and isn't as generous, but it's better than nothing) from a home country even while you live in Singapore. Some countries allow their expats to continue to contribute to their social insurance systems voluntarily, and other countries (notably the U.S.) don't but still have expats who receive (or can legally "engineer") social insurance taxable income.
4. There are also occasions when your employer is posting you to Singapore for an assignment, keeping you (to some degree anyway) on your home country's roster, including on your home country employer's disability income insurance. I had (past tense now) some great employer group DII coverage with an option I exercised to "buy up" to cover a higher percentage of salary, and for a while I was able to hang onto that coverage even while working in two other countries. Sadly, I couldn't keep that coverage, but the coverage was tied to the specific employer anyway, and it's not solely my choice to work for a particular employer. "Portable" DII has that advantage, that it continues when you change employers as long as your time between jobs isn't too long.
5. As I hinted above, give some thought to what happens if your significant other were to become disabled and on the impact to your spouse if you were to become disabled, including
where you and your spouse would
want to be in that event, either event. In other words -- and I've saved the "best" for last -- try to imagine the unimaginable(s), then work backward from there to figure out whether and how you can insure. For example, if almost certainly your household is going move to a house upstairs or across the street from your sister-in-law's house (in Country X, not in Singapore) if your spouse were to become disabled, OK, fine, that's the plan, now figure out whether and how insurance can help. And if you're not sure, OK, fine, mark that down as "not sure/need flexibility" then see whether and how insurance can offer sufficient flexibility.