Paying Taxes With Credit Cards: 10 Scenarios That Might Make Sense

April 15, 2014

It’s Tax Day, and one of the questions I’m asked the most at this time of year is whether paying taxes with a credit card is a good way to rack up points and miles and if so, what credit card to use to maximize your taxes. It would seem like paying your taxes using […]

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What Credit Card Should I Use To Pay My Taxes Off With?

April 13, 2014

Tax time is upon us this week and TPG reader Vick tweeted me asking me what credit card I would recommend to use to pay my taxes. Here is his question: “@thepointsguy If I’m going to pay my taxes is it better to pay with Amex Premier Rewards Gold, Chase Sapphire Preferred or Chase United Presidential […]

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Tax Time Pointers: Earning Points on Taxes

March 17, 2014

It’s tax time again, and as we all prepare our annual statements (that is, if you don’t do it quarterly like many small businesses do), chances are you’re wondering if there are any opportunities to earn points on all those dollars you’re forced to fork over to Uncle Sam. One of the questions I get […]

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Fees Waived For Limited Time on Chase Prepaid Visa Debit Cards – Good Way To Pay Taxes

April 10, 2013

Note: I am not a tax advisor, so before you make any decisions, you need to consult your personal tax professional. Update: You can no longer purchase Vanilla Reload cards using a credit card and Vanilla Reloads are no longer available in Office Depot. Chase is now offering Visa gift cards of denominations up to […]

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Maximize Monday: Making The Most Out of Your Taxes

April 1, 2013

Tax season is upon us and the April 15 deadline to send your money to Uncle Sam fast approaches. Before you write a check, though, I thought it would be a good idea to go over the various other options you have where you can earn points and miles by paying your taxes. In fact, […]

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Maximizing the Delta Suntrust Debit Card

January 31, 2013

Lately we’ve seen lucrative 100,000 and 75,000-point sign-up bonus offers on credit cards, so a simple 5,000 bonus on the Delta Skymiles World Check Card might seem a tad underwhelming. However, the card has a few other qualities that make it a decent option for those who can’t get in on the credit card offers […]

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Why I Paid My Taxes With a Credit Card to Earn Points and Hotel Nights

September 25, 2012

I always get asked if paying taxes with a credit card is a good way to rack up points. My answer is always: it depends on your situation since there are fees involved using credit cards, so the value proposition decreases drastically. However, depending on the size of your bill, it is a quick and […]

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Does it Make Sense to Pay Taxes With a Credit Card?

March 5, 2012

As Tax Day begins to loom, a question I start getting a lot around this time of year is whether it’s worth it to pay your taxes using a points-earning card. Sure, you get the points, but many of the payment services you have to go through in order to do so charge fees that […]

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Amex Issues Revised 1099′s for Unclaimed Gift Chain Prizes

February 28, 2012

Following up on the post a couple weeks ago about Amex sending out 1099s for prizes from their Gift Chain promotion including duplicate ShopRunner memberships, our TPG intern Ryan came across a FlyerTalk thread that at least gives new hope to savvy consumers who took advantage of the promotion that they might not be on […]

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TPG on Fox Business News: The Taxation of Frequent Flyer Miles and Points

February 20, 2012

There’s been a lot of buzz lately on taxing miles and points and I recently got a chance to talk about my position on Fox Business’ The Willis Report. The host, Geri Willis, is a fierce consumer advocate, so I had a feeling we might have a similar stance on this subject. In case you […]

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More Bad News on Taxes and Points: Amex 1099′s Gift Chain Prizes

February 8, 2012

When Citibank sent out 1099’s last month to customers who had received 25,000-point sign-up bonuses for opening checking and savings accounts, the whole points community was up in arms. The tension ahs somewhat subsided a bit thanks to the IRS basically saying it plans to take no major actions on this topic for the time […]

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