If a loan has a prepayment penalty attatched to it would it still be viable to retire it?

It would depend on whether the savings gained by "retiring" the loan outweighed the disadvantages posed by the pre-payment penalty. Most loans have pre-payment penalties which expire after a short period of time. On mortgage loans, the typical pre-payment penalty runs 1, 3, or 5 years.

You need to compare the cost of the repayment penalty and the benefits of having the loan (such as deductible interest) vs. the benefits of paying off theloan such as increase cash flow. Do that analysis and determine the best use of your money.

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