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I've got about 6 loans or so with different payoff times and interest rates. My general strategy is to calculate how much I'd save by paying an extra X per month, always directed towards the loan with the highest interest rate.

However, calculating this is tough by hand because you have to figure out when loan 1 is paid off, then roll the other loans forward to that date, repeat the process, etc, and sometimes certain low-interest loans get paid off naturally before you can reach them to apply +X to it per month, and so on.

Is there anything out there that takes all this into account?

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What you are probably interested in doing is a variant of the Debt-snowball method of paying down your debt. For an online calculator using a method like what you described, check out Snowball debt calculator. Here's the description from the site itself:

Snowballing is all about paying your debts in the correct order. Generally speaking you should attempt to pay off the debts with the highest interest rate first. Some people, such as Dave Ramsey suggest you pay the card with the smallest balance first, that's fine, and can help you feel you're getting rid of the debt quicker, but it's not the most efficient way. This calculator allows you to enter up to 20 different debts with their associated APRs, and the total amount you want to spend per month servicing your debts, and it'll work out the order in which you should pay them together with the monthly payments. [...]   [emphasis mine]

The tool appears to do what you are looking for.

Note: The site is in the U.K. and the currency symbol shown is '£', but if you ignore that and look at numbers only, it ought to calculate reasonable results for other countries.

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Perfect -- thanks! –  AgainstASicilian Sep 7 '12 at 20:54
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The easiest and best option is to create an Excel Spreadsheet to do this for you. I'm sure there are a few budget apps that would do this for you, but their cost is usually too high and they aren't as flexible as a custom Excel Spreadsheet.

Excel includes a Loan Payoff template that you can use as a starter.

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