Point Me To First Class 126. How Much Is a Point Really Worth? A Deep Dive with Frequent Miler’s Greg Davis-Kean
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Jul 28, 2025 
Greg Davis-Kean, a frequent traveler and expert from Frequent Miler, shares his insights on the true worth of travel points and miles. He discusses how to strategically evaluate point redemptions and the psychology behind redemption pressure. Listeners learn when to redeem versus when to wait for better opportunities, plus tips on maximizing hotel loyalty programs and transferable credit card points. Davis-Kean also highlights recent changes, like Chase's points boost feature, and provides guidance on navigating award travel effectively.
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Points Value Evolves Constantly
- Points and miles values fluctuate, but current earning potential often offsets redemption inflation.
- Frequent new opportunities continuously arise, balancing losses with fresh valuable options.
Evaluate Points By Purchase Price
- Evaluate points value by the price you'd pay to buy them, not just redemption rates.
- Aim to get more value from points than equivalent cash back to justify using points.
Choose Transferable Points
- Prefer transferable points over hotel or airline-specific points for flexibility.
- Transferable points allow you to capitalize on emerging travel award opportunities across programs.