The area here (within 1km of HPPS) cheapest is approx $1200 psf at Pandan Valley or The Sierra which set you back $1.5mio (3-bedder). That means you need $600k d/p excl misc like stamp, comm etc. And then, you probably can rent it out for around $3.5-4.5k with a bit of effort. Your mthly would be approx $3.1k (2%/ 30year loan) + Maintenance can probably be covered by your rental income.
But if I have $600k, i would rather pay down my condo and save up for the 20-30% for 2 ppty. There are many ways (les risky financially) to be within 1km of HPPS, eg buying HDB, renting private condo/ hdb. Buying a place, and base on your $7k combine, imo is a stretch and I'm happy you excluded your variable income (assuming your variable is 30% of total income). IMO, its risky because if you cant find a tenant, you will have problem coming with $3-4k (if interest rate goes up to 4%) just to service the loan of this ppty and your hillview condo (which i assume its serviced by your CPF). And from my experience, its really not that easy to find tenants at Mt Sinai area as there r better located and newer condos for tenants to choose. I only stay invested in this area because I really like Ridgewood for its space and huge apt size.
But then again, its really your $ and we do not know what sort of financial backing do you have. Maybe you are working for your dad's SME and thus he pays you a low basic
Ah.....then I say, go ahead man! Haha.....
And then, I would say, go for myer's/ amber's ppty. But of coz the issue of school will come up coz the only school there is Taonan and its darn hard to get into taonan even at phase 2B within 1km (and myer is 1-2km)...in the end, try not to buy ppty for school. If need to be within 1km, rent. Investment purpose, look at other factors as well...(and school might well be a reason coz other parents might rent from you)