“Rely less on the airline to just offer you a good deal,” Mr. Leff said. “Often you want two cards: one that earns multiple points in the category where you spend the most, and one that pairs in the same ecosystem from the same bank that earns 1.5 or two points per dollar.” This means using two cards from the same bank — for example, pairing Chase’s Sapphire Preferred with its Freedom Unlimited card to pool their earned points.

This flexibility proves crucial as sweet spots move between programs. Virgin Atlantic, for instance, charges just 90,000 miles for ANA first-class flights to Japan. That same seat would cost 220,000 United miles. Even Flying Blue, Air France-KLM’s program, still offers business class to Europe for 60,000 points — notably less than what many U.S. carriers charge. Premium Amex and Chase credit cards allow points transfers to multiple airline programs — meaning cardholders aren’t tethered to one airline’s availability.

For families seeking multiple premium seats, timing becomes crucial. “If you’re going to Europe, you may be pleasantly surprised with Flying Blue because they offer multiseat availability even at their saver rates,” Mr. Qin said, referring to the lowest-priced award tickets airlines offer. Some carriers, like Japan Airlines, often release blocks of award seats within two weeks of departure.

Mr. Leff recommends booking what’s available on your primary airline, and then watching for better options. Since most programs now waive change fees on award tickets, you can switch if partner space opens up. Just note that once you transfer flexible points to an airline, you can’t transfer them back.

Perhaps most important: Don’t let the perfect be the enemy of good.

“Remember, the best points are what’s best for you. If you need to book an economy-fare flight because that makes sense, do it,” Mr. Qin said. “Don’t always shoot for the perfect or the ideal, because you’ll just never use your points and they’re going to devalue.”

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