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The trick is most of these are auto-assessed, you don't apply blindly for each. Practical approach: 1) log in to the Supportgowhere / govbenefits site with Singpass, it consolidates what you're eligible for based on your profile, this is the single best starting point, 2) CDC vouchers, everyone with a household gets them, claim via the redeemsg link when announced, 3) GST Voucher (cash/MediSave/U-Save), auto-assessed on income and property annual value, no need to apply, 4) Baby Bonus (cash gift + CDA co-matching), you enrol usually at the hospital or via the LifeSG app after birth. For a middle-income family with a kid and HDB you likely qualify for CDC vouchers, some GST Voucher components, and Baby Bonus. Check Supportgowhere with your Singpass, it's tailored to you, and verify each scheme's current criteria on the official pages since amounts change yearly.