I have a very strong and simple point of view about this, so here it is.
CPF LIFE never guarantees a bequest. If you want to guarantee (or virtually guarantee) a bequest, the only part of CPF that does that reasonably well is MediSave. So, top up somebody's MediSave Account, and that'll pretty well assure a bequest, to the CPF member's nominee.
The only thing CPF LIFE can do is to provide a lifetime stream of income to the account holder. In other words, the only promise it can deliver to anyone is as longevity insurance, to provide some level of income to prevent destitution.
OK, given that -- that the only thing CPF LIFE can assure is to prevent someone from completely outliving his/her savings -- then why not make CPF LIFE the very best longevity insurance it is capable of being? If you're going to enjoy a symphony concert, enjoy the best, with the best violin players, the best clarinet players, the best conductor, with your favorite symphonic selections.... Best, best, best.
So, what's best? Well, simple: start your payouts at age 70 (if you can afford it), and make those payouts Escalating, which is the only CPF LIFE payout plan that does anything to combat inflation. Inflation is real, and you must have a plan to combat it. The Escalating Plan does that.
There are those who argue that you can get $5 more (or whatever) of interest if you do something else, and if you live precisely 92 years and 3 months (or whatever). That's frankly nonsense. Everything that isn't a life annuity can play those games, including parts of CPF such as Ordinary and Special Account funds if you're so inclined. But this is not a game. CPF LIFE can only be a life annuity and only assure that. It can never assure anything else. And with that assurance of real spending power for life (Escalating Plan), however long that life lasts, comes power. As a notable example, if your CPF LIFE Escalating Plan income is sufficient enough to support your modest lifestyle (it has to be modest since CPF LIFE is never lavish), then you can safely afford to give away every other bit of wealth you have -- to enjoy life with your kids, grandkids, etc. while you're all still alive. It gives you the power to give away your bequest today, now, and not wait until you're dead and hope that there's something left over.
Money has zero value to someone who's dead. The ideal outcome is that you enjoy every day of your life, with an adequate (or better) real income for the rest of your life, and give away all your surplus to your loved ones and/or to whatever causes you care about, and do that NOW, to enjoy that generosity while you're still alive, together. The CPF LIFE Escalating Plan starting from age 70 provides the maximum possible foundational assurance of being able to achieve that ideal, blissful outcome. And it's the most attractively priced longevity insurance available for Singapore dollars and one of the most attractively priced longevity insurance offers in any currency.
Anyway, I think it's very, very simple. Now, I do allow a few exceptions to this simplicity. Here are the big ones:
1. If you're already in line to collect lots of escalating annuity income from other governments, private pensions, etc. then maybe you minimize CPF LIFE in certain ways because you feel you have "too much" longevity insurance already.
2. If you're diagnosed with a terminal illness and have good or better visibility on precisely when you're going to die, maybe you make certain other CPF LIFE decisions.
3. If you hate the government and want to make a political statement (that nobody will hear) because that'll make you personally feel better for some odd reason, OK, have fun. Some people have weird sources of pleasure.
4. CPF LIFE is not designed as a joint/survivor annuity, and when you have a spouse/partner who is almost certainly going to outlive you, and if your household is of limited means, you might do some things a bit differently.