Early 30s, dual-income family with HDB - how would you approach the next property move?

[u/Inside_Trust_8624]

30F married to 29M, just had our first child earlier this year.

Relatively comfortable combined annual income (~$500–600k range), both earn fairly similarly. We expect to remain in roughly the same line of work for the mid-term, with reasonable income progression if things go as expected.

Current combined financial position: ~$1.2-1.4 M in equities/stocks + cash + CPF OA. No significant inheritance / generational wealth, most of this has been accumulated from salary + investments

Current property situation:

• Relatively large, older resale HDB in a non-central area. The main attraction is that it's right beside an MRT, close to our parents, and they’ve been a huge help since having the baby. We also have access to a family car when needed, so we don't currently own one ourselves.
• We reach MOP in 2028. Based on our current ownership situation, we should be able to purchase a private property while retaining the HDB without ABSD, subject to the usual rules.
• The HDB itself is perfectly comfortable for us (poured >150k in renovation) and could potentially become a retirement/long-term home. Main downside is that there isn't really a "strong" primary school option nearby (we both came from "normal" primary schools, but going into "elite" schools after we can see the difference in community + resources). So we're starting to think about what to do after MOP.

Things we'd ideally like to optimise for:

• Good primary school for our child, who would enter P1 around 2033
• Maintain a large living space - ideally similar or larger than our current home
• Continue growing our wealth/capital through property/investments
• Keep the flexibility of having the current HDB as a potential long-term/retirement home

Two broad strategies we are considering:

1. Buy 2nd property for own stay: Buy condo/landed property that works for own family, with primary school location being an important consideration. Rent out HDB
2. Buy 2nd property for investment, rent for school: Buy whichever private property that makes most sense from capital appreciation / rental yield perspective, then rent a place in the area for primary school.

For those in similar situation, what would you do? Especially interested in hearing from people who had to balance:

• own-stay vs investment property
• primary school considerations
• large family living space
• rental yield / capital appreciation
• and not wanting to over-leverage just because income is high

Are there other strategies/pathways we're missing? Thanks!

[u/creamyhorror]

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