If I lose my job, I have 30 days to pack my bags and leave the country.
That’s true. However, if you have a fixed monthly salary of at least $12,000/month, you could apply for a
Personalised Employment Pass. You’re allowed a maximum of one PEP per lifetime, and a PEP is good for 3 years. At the end of the PEP you have three options: (a) drop down to a EP, (b) rise up to PR, or (c) leave Singapore.
PEP holders are effectively self-sponsored EP holders, and a PEP holder can stay in Singapore for up to 6 months after cessation of employment. (Although a bout of unemployment that long would likely trigger an eventual early loss of your PEP, with the three options listed above.) PEP holders can also sponsor dependents for DPs.
It’s a quirky immigration status that’s somewhere in between an EP and PR. In practice, if you meet the income qualification (which could change, although probably not for people holding PEPs), you could try to apply for a PEP if your current employment seems wobbly. You have to be in employment to apply and to pick up your PEP, though, so it cannot be too wobbly. But if your goal is to stay in Singapore for at least another 5 to 7 years, you want to be a little careful about when you apply.
I think you have up to 6 months to pick up a PEP after approval, so you can stretch the total anti-wobble protection out to roughly 3 years and 7 months, figuring 1 month for the application decision, 6 months before you pick up the PEP, then 3 years once you do pick it up.
If you’re successfully on a PEP then I suppose you could attempt one more PR application, at about month 20 of your PEP. Maybe the PEP counts for a tenth of a point or whatever. Who knows.
If you’re not at $12K/month or above then please ignore all the above, at least for now.