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What do you think? How much, if any, should I nab from my e-fund to reduce my student loan obligation?

I would hold off on raiding the e-fund until you've bought the ring and sold the condo. That will give you a better idea how much you have. In the meantime, if there's extra money from bonuses and other unexpected sources, I would start an on-line savings account dedicated to wiping out your student loan. By keeping the money, you get the benefit of the interest that will accrue.

Once the ring has been bought and the condo sold, wipe out the credit card portion of the debt. Direct that $175.00 a month toward the on-line account until you're confident about how things will be, and you are sure that you won't need to buy a new car (I know that you feel yours will last, but there are a lot of idiots out there on the roads, and if someone runs a red and creams you, you aren't going to get a lot of money from insurance).

When you have enough in the savings account to wipe out the loan, pay it. But I wouldn't throw the money at it bit by bit when you can get the value of the accrued interest, and then wipe out the entire debt at once.

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