Pay Taxes, Earn Big Rewards


You may not ever hear two people who are more excited about paying their taxes than Greg and I sound on this week’s Frequent Miler on the Air. That excitement stems from the fact that tax time presents opportunity to meet spending requirements and earn outsized rewards. On this week’s episode, we talk about your best strategies for maximizing your, ahem, returns.

Elsewhere on the blog this week, we dedicate some digital ink to Air Canada Aeroplan in light of the monster Bilt Rent Day promo (which was enough to push me over the edge to finally add a Bilt card in my household), Greg pulls off an awesome experiment with Flying Blue Stopovers, and Stephen and Tim reveal which card is in all of our actual daily-carry wallets for the same purpose. All that and more below.

Watch, listen, or read on for more from this week at Frequent Miler.

Frequent Miler on the Air Podcast

00:01:35 – Using ChatGPT to squeeze $300 from the Ritz-Carlton card (Giant Mailbag)
00:10:57 – Capital One Spark Cash Plus: 2% Everywhere (Card Talk)
00:16:30 – Pepper App (Crazy Thing)
00:23:07 – Paris Hilton’s Slivingland on Roblox: Win 111,111 Hilton points, Diamond status (Mattress Running the Numbers)
00:31:30 – Free Delta stopovers via Air France / KLM Flying Blue (Award Talk)
00:36:10 – Luxury stays (Leading Hotels of the World) thanks to Citibank (Award Talk) Read
00:41:07 – Main Event: Pay Taxes, Earn Big Rewards Read more:
00:41:37 – Paying Federal taxes with a credit card
– Why pay a fee to use a credit card?
00:54:33 – What about other taxes?
|00:58:06 – Is it OK to overpay taxes?
00:59:52 – Does it make sense to pay quarterly estimated taxes this way?
1:00:26 – What to do when the payment processor doesn’t like my business credit card? 01:02:51 – 90 days to use ’em or lose ’em: Where would you transfer your points? (Question of the Week)

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This week on the Frequent Miler blog…

75%-150% transfer bonus to Air Canada Aeroplan with Bilt Rent Day Promo

Bilt Rent Day

Saddle up: on February 1, 2024, for one day only, Bilt Rewards is offering a 75-150% transfer bonus to Air Canada Aeroplan. That’s a fantastic bonus to a highly valuable rewards currency. Personally, I’m planning to transfer what Bilt Rewards points I have to Aeroplan on the 1st because I just can’t see not taking advantage of such a monster bonus to a rewards program I love. I am excited to see Bilt continue to offer these big bonuses and now to such a valuable program — and taken in conjunction with the announcement this week of a fresh $200m in funding based on a $3.1B valuation and the addition of a former Amex CEO and the commissioner of the NFL to the board, it sounds like good things are going to continue coming from Bilt.

Best uses of Air Canada Aeroplan points (ways to maximize that 75%-150% Bilt transfer bonus)

a hand holding playing cards

Wondering why I’m excited enough to speculatively transfer all of my Bilt points to Air Canada on February 1st? In this post, I cover the various best uses of Aeroplan points and how you could use them in conjunction with this transfer bonus to pay just 5K Bilt points for a ticket from the west coast to Hawaii, 58K Bilt points to fly 18+ hours in first class with Oman Air and Lufthansa along with a few hours in business class to get from Africa to Los Angeles, 5K Bilt points to get to the remote reaches of the Northwest Territories in Canada and a lot more.

Air Canada Aeroplan Complete Guide

a map of the world
The United search results I found give me hope for really cool routings — and for finding domestic award tickets.

If you need just a little bit more Air Canada in your life, we also updated our complete guide to Air Canada Aeroplan. This post has all the ways to earn miles, the full award charts for your research reference, elite status benefits, and a lot more.

90 days to use ’em or lose ’em: Where would you transfer your points?

a finger pressing a green key on a keyboard

Did I imply that we were done with Air Canada Aeroplan? Well, this post isn’t directly about Aeroplan, but rather it was written in response to an interesting question posed by a reader: In light of the new law in New York State that issuers must give you 90 days to use your accumulated rewards in the case of a shut down, where would you transfer your points if you had 90 days to use them or lose them? Funny enough, Aeroplan was a top pick for me from a couple of programs, though it wasn’t the only pick I put forth in this post. On this week’s podcast, Greg shares his thoughts about this question during our question of the week segment.

Flying Blue Multi-Stopover Experiment

Man examining a globe through a microscope

Speaking of Greg’s thoughts, he’s been putting a lot of them into Air France / KLM Flying Blue’s free stopovers. Ever in search of the limits, Greg went about seeing how the process works for booking a Flying Blue award with multiple stopovers in a single direction. The short story is that it’s possible! It does seem to probably kinda sorta increase the price of the award some, but since Flying Blue doesn’t exactly have a reliable award chart and since it’s not exactly possible to price out a specific circuitous routing to know what the price “should” be, we can’t exactly surmise how much (if at all) the stopovers increase the cost of the award. What we do know is that it looks like this has the potential to work really well for those willing to put in the effort.

What I learned watching Greg book Flying Blue awards on the Air France website

How to find flying blue awards on air france

Carrie has been putting in effort in learning (or perhaps re-learning) all about award booking by watching Greg’s how-to series. This short post provides some notes, but you’ll definitely want to watch the video if you’re not terribly familiar with booking Flying Blue award tickets.

Delta SkyMiles Complete Guide [2024 Edition]

Delta Air Lines Greg in Delta One

Delta made many changes to its elite status program that took effect in January 2024. As a result, Greg has updated this complete guide with everything you need to know about Delta SkyMiles in 2024 and beyond.

Sampling Leading Hotels of the World (LHW) thanks to Citi ThankYou Rewards

Brazilian Court Hotel LHW Yacht

Switching gears to hotels, Greg recently had a chance to give leading Hotels of the World a spin. You may remember that LHW was added as a Citi transfer partner last year and the program looked like a way to get pretty good value out of your Citi ThankYou points. As it turns out, this partnership is even better than expected given the room upgrade and other benefits that Greg got just by becoming a member of the loyalty program. I thought this post did a fantastic job of separating the valuable intel you need to know to go after this opportunity from the disappointments of the specific property where he stayed. I think I actually might have focused more on some of the shortcomings Greg notes of the specific hotel (given the price point!), but I think Greg was wise to focus more on the LHW process itself since that is far more applicable to far more of us.

What’s in Stephen’s wallet? 2024 edition

Stephen's wallet 2
I still have the same Big Skinny Wallet that I’ve had for several years

Stephen has the largest wallet of the Frequent Miler team. That’s not to say that he has the most cards — in a recent Ask Us Anything, we discovered that Greg has around 80 cards in his household — but Stephen seems to carry far more cards than the rest of us. That makes some sense since he is a full-time traveler (and has been for years), so he likely runs into maximum opportunity for bonus categories.

What’s in Tim’s Wallet? 2024 Edition

Tim's Wallet

Tim rounds out our wallet posts. Many readers loved his approach to Player 2’s wallet and I have to admit being a bit intrigued myself. I like his use of a Premier card in that Player 2 wallet. On the one hand, it initially didn’t make sense to me given the fact that his Player 2 carries a Wyndham Earner Business card for 8x gas. It would therefore seem like 4x dining and grocery with an Amex Gold card would make more sense. However, Tim made a great argument: we earn enough Amex points from welcome bonuses and retention bonuses that I would probably stand to benefit by rotating the Premier into Player 2’s wallet to earn some Citi ThankYou points since we’re otherwise very light in that department.

That’s it for this week at Frequent Miler. Don’t forget to keep an eye on this week’s last chance deals.

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