What government payouts am I actually eligible for? So many schemes, so confusing

Supportgowhere is genuinely the answer to your exact question, you just log in with Singpass and it lists out what you can get based on your real profile, income, housing, family, instead of you trying to piece together a dozen scattered scheme pages and guess which apply. It saved me hours of confused googling. The other thing that trips people up is realising that most of these payouts are automatic once you qualify, you don't fill in a separate form for each, but you DO need your bank details, ideally PayNow linked to your NRIC, set up correctly so the money actually reaches you promptly instead of getting stuck. Do those two things, check Supportgowhere and sort out PayNow-NRIC, and you've covered ninety percent of it.

Link your PayNow to your NRIC, this one small admin step makes a surprising difference because so many payouts, GST Voucher cash, various support schemes, are disbursed via PayNow-NRIC and land in your account instantly the day they're released, whereas without it you wait for slower GIRO setup or a cheque, or worse the money sits undisbursed. It takes two minutes in your banking app, you just register your NRIC as a PayNow proxy to your preferred account. I set this up years ago and every payout since has just appeared automatically with a notification, zero chasing. For a family juggling a kid and a household, that automatic reliability is worth the two minutes. Do it before the next round of payouts is announced.

For Baby Bonus specifically, note that you do actively enrol for it rather than it being fully automatic, easiest via the LifeSG app after your child is born (or at the hospital), so don't assume it just happens. And the Child Development Account (CDA) part is where the real value hides, the government co-matches what you deposit dollar-for-dollar up to a cap, which is essentially free money for your kid's expenses, so top it up to the cap to grab the full match rather than leaving it on the table like a lot of tired new parents accidentally do. Since you've got one kid already, check whether you fully claimed the CDA match. Verify the current match caps on the official Baby Bonus site, they've been revised.

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.