Mailbag #8: Earning More Points, Top Listener Hacks, Monitoring Price Drops, Paying Taxes on a Credit Card and More

Credit Card Rewards

Chris Hutchins shares strategies for maximizing credit card rewards, emphasizing the importance of choosing the right card based on one's spending habits. He compares the Bank of America Premium Rewards Visa and the Chase Sapphire Reserve, highlighting that while the former offers a straightforward cashback option, the latter provides more flexibility with points transfer to airline and hotel partners 1. Chris also discusses the potential benefits of paying taxes with a credit card, especially when aiming to meet minimum spend requirements for sign-up bonuses 2. He advises prioritizing sign-up bonuses over regular points accumulation, as they often offer greater value 3.

If you're trying to meet a minimum spend on a sign-up bonus, or if you're trying to earn some points in a program really quickly, especially if you're trying to do that with a card like the Venture X, where you can earn two points per dollar and potentially make those points worth anywhere from one and a half to three.

--- Chris Hutchins

Ultimately, the choice of card and strategy should align with individual financial goals and spending patterns.

   

Companion Pass

Chris explores the Southwest Companion Pass strategy, a valuable tool for frequent travelers. By earning 135,000 points in a year, travelers can secure a Companion Pass, allowing them to add a companion to their flight for just the cost of taxes 4. He explains the timing of earning these points is crucial, as achieving the pass early in the year maximizes its benefits for nearly two years.

The trick here is that when you earn it, you get it for the rest of the year and the following year. So you really want to make sure you earn it as early in the year as possible.

--- Chris Hutchins

Chris also suggests a joint strategy with partners, alternating the earning of the Companion Pass to extend its benefits over several years. This approach requires careful planning and spending but can significantly reduce travel costs.