Do you think you (and your family) will find it affordable to retire in Singapore? (Asking those between 20s-50s). For those already in 60s, do you find it affordable to retire in Singapore and why?

It's not a matter of finance but community. Singapore is actually very comfortable as most have pointed, to the context of cooking and transport. Community vegetable rescue and PA related gathering is often a bonus to sustain these communities being together. Aside from mortgage and liability free, actually the park and connectivity is a HUGE factors that other countries are struggling to find.

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Case in point, you can have all the financial means to retire similarly in Malaysia but you need to drive and reach to those parks.

I think daily basic expenses such as food, transport are very affordable.

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Medical is another thing altogether but try to hedge with insurance.

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I am assuming a fully paid up flat.

Depends a lot on lifestyle expectations and housing. Singapore can be affordable if home is paid off and spending is kept simple, but gets expensive with healthcare and supporting family.

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Most people seem to plan around CPF as the base, then top up with savings, investments, maybe some rental or part-time work. Not so much about rich retirement, more about steady cash flow and managing expenses.

Retirement in Singapore is quite possible if one has been executing his/her financial plan based on income and dividend reinvestment. You need to define what is the right retirement income generated from your passive income assets. For me, $5k per month is more than enough for my family. It may not be true for your case if your expenses are large. Trim your expenses until you find it comfortable without much sufferings.

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You will need to live below your means for the first 10 years before you even see any fruits of your plan. Don't waste money on any insurance, except for maybe 1 or 2 Life Polic(ies) and Hospitalization plan with Rider. Unfortunately, the latter has just become unattractive too because of an obvious reason; someone has been manipulating it politically and shifting it against the population.

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Allocate your investment capital at the right time. Now is not the time to allocate investment capital as the global market is about to collapse. Buy strong dividend stocks only during market panics and crashes. Most of the time, leave your money in safe and income-producing assets (fixed income assets) that are protected from defaults no matter how bad the market can crash. Compound those interests if you cannot find any good assets to invest.

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Allocate at least 5-10% of your investment capital on asymmetric assets like crypto (especially bitcoin). Sell half when they have doubled. Buy again (with that half) when there are market panics. I personally will not sell bitcoin for whatever reasons. Rinse and repeat. This formula can produce outstanding 6-figures to 7-figures returns over a period of 4 years consistently, with just $10k starting capital. You can use this method with institutional-grade stocks with high volatility to capture asymmetrical upside and downside risks.