Maximizing Points from Tax Payment

Old Feb 10, 19, 5:15 pm
  #1  
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Maximizing Points from Tax Payment

Have a hefty tax payment coming. What is the best way to maximize Chase UR points? I carry Ink Biz (5x for office supplies) and Sapphire Pref.
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Old Feb 10, 19, 7:34 pm
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Originally Posted by casterpix343 View Post
Have a hefty tax payment coming. What is the best way to maximize Chase UR points? I carry Ink Biz (5x for office supplies) and Sapphire Pref.
What is "hefty"? For some, 3 digits is hefty while for others, 6 digits is significant. And it matters since you can wind up paying lots of money for your points.
If your taxing entity allows you to pay with MOs, then your cost if using SMGCs and WM is around 0.8%. So you can do your own calculations as to the value of your points generated by paying with MOs. I think that without special situations (such as fee-free GCs), the costs only rise outside of SMGCs and WM MOs.

On the other hand, if you are paying Federal taxes, they will let you pay with a CC but there is a "convenience fee" which can be (as I read it) as high as 2.3% of the principal. When your taxes are high that means you are paying lots of cash for your points.

However, it's your call to decide if it is worthwhile for you.
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Old Feb 11, 19, 8:57 am
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I just paid my taxes with a new card to hit minimum spend for bonus (will actually pay again in March with another card and hit 2x min spend). It's going to cost me an extra $70-80 or more vs buying debit on sale at OM/[email protected] or doing the SM route and paying with those, but it gives me peace of mind that I can work with CC company if there is any issue with payment.

Have you thought of opening something new up (Airline card/hotel card/etc..) that you can use for this spend?
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Old Feb 11, 19, 4:39 pm
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Extensive discussion here:

Paying USA income, property or other taxes with a credit card

Unless you are overpaying, this isn't Manufactured Spending.
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Old Feb 11, 19, 9:49 pm
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Originally Posted by bigshooter View Post
I just paid my taxes with a new card to hit minimum spend for bonus (will actually pay again in March with another card and hit 2x min spend). It's going to cost me an extra $70-80 or more vs buying debit on sale at OM/[email protected] or doing the SM route and paying with those, but it gives me peace of mind that I can work with CC company if there is any issue with payment.

Have you thought of opening something new up (Airline card/hotel card/etc..) that you can use for this spend?
Looking at about a 10K tax payment.

So your suggestion makes sense. What cards did you sign up for?
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Old Feb 12, 19, 10:25 am
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Originally Posted by casterpix343 View Post
Looking at about a 10K tax payment.

So your suggestion makes sense. What cards did you sign up for?
I used Citi AAdvantage cards for this one since I'm locked out of Chase apps for a while. What airlines and/or hotel chains do you stay at?
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Old Feb 12, 19, 5:51 pm
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Trying to hit top tier with AA this year so might just sign up with Citi.
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Old Feb 14, 19, 8:59 pm
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Originally Posted by casterpix343 View Post
Trying to hit top tier with AA this year so might just sign up with Citi.
Unless you can get multiple Citi cards by 4/15 make sure you spread things around. If you enjoy Marriott or Hyatt the branded Chase cards (or Sapphire Reserve) are fantastic. Always get Chase cards first as they are subject to no more than 5 approvals in 24 months.

In your case it makes sense to get 3-4 cards that have $3000 MSR to maximize things.
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Old Aug 1, 19, 5:48 pm
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2 questions:

1. Does anyone know if you can use Simon Mall VGCs to pay estimated taxes online at Official Payments, Pay USA Tax, and Pay 1040?

2. When does the window for paying 3rd quarter Federal estimates online open? Is it August 1 or August 15, or some other date?

Last edited by GetawaysRus; Aug 1, 19 at 7:54 pm
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Old Aug 1, 19, 7:26 pm
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2. Used to be 45 days before the deadline but this year it’s 30 days (maybe 31).
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Old Aug 6, 19, 1:12 pm
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Originally Posted by GetawaysRus View Post
2 questions:

1. Does anyone know if you can use Simon Mall VGCs to pay estimated taxes online at Official Payments, Pay USA Tax, and Pay 1040?

2. When does the window for paying 3rd quarter Federal estimates online open? Is it August 1 or August 15, or some other date?
1) Not sure about using Simon.
2) Q3 deadline is 3rd payment ................. Sept. 16, 2019.
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