As mentioned in this old thread, only Singapore-issued Diners Club cards allow direct CPF top ups. You’ll receive no Diners Club points for CPF top ups, but you’ll get a bit of free float since the payment only comes due when the charge appears on your Diners Club statement.
I’m not aware of any $10 fee when you do this. I’m not sure where that part came from in this old thread.
Hypothetically you could take a cash advance from another credit card to top up CPF, but that’d be very expensive. Maybe if you were rolling over a credit card balance to a new card because you got a 0% interest offer with no fees — a rare offer but not unprecedented — that sort of maneuver (cash advance on old card, rollover to new) might make a little sense. But it’s tricky to pull off. And you’d still be better off using a Diners Club card as the “old” card in this role.
All Diners Club cards issued in Singapore have annual fees after the first year, so you probably wouldn’t want a Diners Club card unless there’s some other benefit that’s big enough to offset the eventual annual fee, or you’re doing this all within the first year of card membership. You can pay the annual fee using points if you’ve accumulated enough.
The Diners Club Ace card, with a $500 credit limit, happens to be Singapore’s lowest income threshold credit or charge card (minimum $16,000/year income to qualify). It’s a pretty good card for those who struggle to qualify for other cards, although CIMB’s AWSM credit card is better overall if you can qualify. Yes, you can use the Ace card to top up CPF, up to $500 at a time.