"Old" and "leasehold" - two words that make most Singaporean homebuyers cringe. No matter how many experts explain that leasehold properties can outperform freehold ones, there's an undeniable emotional resistance. Deep down, people want to believe they're investing 25+ years of their hard-earned money into something lasting. So what would possess three homeowners to go against the grain and purchase not just leasehold condos, but older leasehold properties? Their surprising reasons might change your perspective.

1. The Self-Employment Dilemma: When Affordability Trumps Ideals

For many dual-income couples where both partners are self-employed, the dream of owning a freehold property often collides with financial reality. Traditional lenders typically view self-employed applicants as higher risk, offering smaller loan amounts or requiring larger down payments. This creates a perfect storm where older leasehold condos - with their significantly lower price points - become not just an option, but sometimes the only viable path to homeownership.

One couple we spoke to, both freelance designers in their late 30s, found themselves repeatedly outbid for newer properties in their desired neighborhoods. "We kept getting priced out of every new launch," shares the husband. "Then we discovered this 20-year-old leasehold development that was nearly 30% cheaper than comparable freeholds nearby." The trade-off? They had to compromise on some modern amenities and accept a shorter remaining lease.

Financial advisors note this isn't uncommon: "For self-employed buyers without consistent CPF contributions or fixed monthly income statements, older leaseholds often represent the sweet spot between location affordability and acceptable depreciation rates," explains property analyst Rachel Lim.