Weekend Edition / Dear Ohad...
The points game isn’t dying — it’s evolving. But if you’re still playing by last year’s rules, you’re losing value every day. This week’s #DearOhad is your no-BS guide to surviving devaluations, dodging fee hikes, and making smarter moves while everyone else panics.

United just devalued again. That’s three times this year! Is dynamic pricing getting worse, or am I just noticing it more?
—Devalued in Des Moines
Dear Devalued,
You’re not imagining it. United has now quietly raised award prices for international business class redemptions — again. Europe from the East Coast is creeping toward 100K one-way, and partner redemptions (like Lufthansa or ANA) are inching up too. Welcome to the age of dynamic disappointment.
The real shift? Airlines aren’t just raising prices. They’re removing predictability. Instead of publishing new charts, they’re letting the algorithm decide — and that algorithm drinks jet fuel for breakfast.
ProTip: Lock in international partner redemptions 6–11 months out, especially via non-dynamic programs like Avianca LifeMiles or Air Canada Aeroplan. Don’t wait until prices “settle” — they’re not going back down.
I’m sitting on 300K Amex points but scared to redeem. Everything feels like a bad deal now. What gives?
—Frozen in Fresno
Dear Frozen,
Points are like avocados — they don’t get better with age, and if you wait too long, you’re left with mush. But I get it. Amex Membership Rewards redemptions can feel underwhelming if you’re staring at gift cards or portal pricing. That’s not where the juice is.
Instead, look toward international business class transfers. ANA to Japan? Virgin Atlantic to Europe? Iberia from the East Coast? Still exceptional deals — but you’ve got to know where to dig.
ProTip: Stop hoarding. Start researching. Every month you wait, the airlines tweak the rules. If your trip is 4–10 months out, transfer and book now. Stashing points is no longer the smart move — using them is.
My Amex Platinum renewal is coming up. Should I cancel now before they raise the fee?
—On the Fence in Fort Worth
Dear On the Fence,
Hold the scissors. We’re likely weeks away from a major refresh — and if Amex follows their usual script, you’ll want to see the full picture before you cancel. Yes, a fee hike is probable. But there may be upgraded credits or elite benefits that make the higher cost worth it — especially if you travel frequently.
Remember: once you cancel, it’s harder to get retention offers or product-change options. Let the news drop first, then make your move.
ProTip: Call now and ask for a retention offer without canceling. If you’re offered $200–$300 or more, and you still get the upcoming refresh, you’ve hedged your bet. If not? You can always downgrade later.
If Chase, Amex, and United are all getting stingier… where should I be earning my points now?
—Strategy Shift in Santa Cruz
Dear Shift,
Great question. We’re in a transition period — and the best players are pivoting, not panicking. Focus your earn on flexible currencies that (a) transfer to strong partners, (b) avoid dynamic pricing, and (c) offer consistent value.
Right now? Here’s where to lean:
- Chase: Still solid for Hyatt and Air Canada Aeroplan. But don’t hoard — transfer with intent.
- Amex: Best for ANA, Virgin Atlantic, Iberia, and business owners racking up big spend.
- CapOne & Citi: Underrated transfer partners, great for international plays and emerging sweet spots.
- Bilt: If you pay rent or dine out often, Bilt is becoming a sleeper MVP with high-value partners.
ProTip: Build around where you want to go, not what your inbox tells you. Let your dream trip dictate your strategy, then align your earning to get there faster.
I’m overwhelmed. Should I just get a 2% cashback card and call it a day?
—Simplifier in Seattle
Dear Simplifier,
If you don’t fly business class, don’t want to deal with transfer partners, and value simplicity over optimization — yes, go cashback. That’s a smart move, not a surrender.
But if you’re spending $50K+ per year, traveling for work, or planning one or more international trips annually, cashback will almost always undershoot the upside. Points have complexity, but they also have leverage.
ProTip: Try a hybrid model. Use a 2% card for everything not in a bonus category, and a flexible points card for dining, travel, or business spend. That gives you the best of both worlds without the headache of going all-in.
What should I actually do this weekend?
—Ready to Act
Dear Ready,
Here’s your short stack for the week:
- If you’ve been eyeing the Chase Sapphire Reserve, this might be your last call before the fee hike. Move now.
- If your Amex Platinum renewal is within 90 days, call for an offer. Don’t cancel just yet.
- Got a big Chase or Amex point balance? Stop waiting. Pick your trip, and transfer before the programs change again.
- If you’re feeling stuck, do a 15-minute audit of your top 3 cards. If you’re not getting at least 2¢ per point or $1K+ in travel value annually, something needs to shift.
ProTip: Great redemptions don’t come from luck — they come from action, timing, and a little help. Stay proactive, and let the banks chase you for once.
Until next time, may your points stay powerful, your cards earn hard, and your travel be better than advertised.
Got a points panic, card crisis, or lounge letdown?
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