Can you not save the extra money (if not spent or needed for the time being) from Standard as top-up to your RA and becomes bequest or additional payout whenever needed?
A roll-your-own Escalating Plan, let's suppose. That is, you take the Standard Plan but siphon off exactly the number of dollars difference between the Standard Plan and Escalating Plan (while the former exceeds the latter) and plow it right back into one's Retirement Account to boost the payout, loop, repeat.
I'm willing to entertain the notion if you've got some math that suggests it works. But I don't think that math is going to work with the possible exception of this combination:
* Below the Full Retirement Sum (i.e. qualify for tax relief with top-ups)
* Have taxable income (i.e. can benefit from tax relief with top-ups)
If you can churn CPF LIFE payouts back into the Retirement Account with substantial tax relief, to get two bites at the apple as it were, that might be interesting as a mathematical curiosity anyway.
There's some interest loss associated with the "minimum balance in the month" CPF interest calculation method when you're roundtripping funds out of CPF back into CPF. But another bite at tax relief could overcome that, maybe. (Would have to see the math, and it's difficult math.)
One problem with condition #1 is that CPF LIFE payouts are never lavish, and they're particularly non-lavish below the FRS. Also, ending up well below the FRS probably means you didn't make the most of top-up tax reliefs available in prior years, so this scenario is threading a difficult needle. And if you have taxable income (chargeable income above $20,000) then you're not too income poor, and longevity insurance is really centrally focused on defending against destitution.
There's a little bit of risk here I should point out since the RA interest rate is not guaranteed but the Escalating Plan's 2% annual increment is guaranteed, atop the actuarial base. That's probably not a lot of risk, but there is some. On the other hand, if the RA interest rate happens to rise (which would/could happen in a high inflation spell), you'd collect a little upside there.
Anyway, it'd be a fun little exercise to run the numbers, just as a possible quirky little corner of CPF LIFE that isn't going to be realistic to execute.