Wah, a few of us in my mum group actually discussed this quite recently, the general consensus is that signing up for the supplement at 30 is smarter than waiting, because premiums are locked in at your entry age and don't increase as you get older, so the total premiums you pay over your lifetime actually work out cheaper compared to someone who starts at 40. Someone in my mum group mentioned that the base CareShield Life premiums for women start around $253 a year at age 30, and you can top it up with a supplement to get that higher monthly payout of $800 to $1,500 if you become severely disabled, all payable through Medisave, so no cash outlay. Some mums love the peace of mind it gives, though a couple had questions about the eligibility criteria for claims and wanted to make sure they understood exactly what counts as "severely disabled" before committing. Definitely worth sitting down with a licensed advisor to go through the fine print properly before you sign up!