Jill on Money: Debt pay down vs investing, Apple

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As we close out July and enter the dog days of August, "Jill on Money" listeners confront an age-old question: When is debt pay down preferable to investing?

The answer depends on your personal situation, of course. For Lauren in MA, her free-cash flow is better used to beef up her retirement savings, while for Phil in VA and Wesley in CA, they are better off focusing on paying down student loans.

One note on Wesley's situation-he wants to help out his parents, who are struggling financially. Perhaps one of the best things to do when confronting this situation for parents, adult children or even dear friends, is to pay for fee-only financial planning on their behalf. Check out NAPFA.org to locate a professional in your neighborhood.

We fielded allocation questions from April, who wanted to understand the differences among bond funds; Thaddeus from Louisville is weighing whether to move $200K in CDs to a managed account with a broker; and Doug from Michigan, who owns 5 different asset allocation funds.

David from Boston rounded out the show with a great problem: he was fortunate enough to invest in Apple stock a long time ago and has now amassed a staggering $2 million in the company. We help him figure out how cash-in on that winning bet.

Here are web sites and resources mentioned in this week's show:

-- Jill's Blog

-- NAPFA: National Association of Personal Financial Advisors (fee-only advisors)

-- Best CD Rates

-- E, EE and I Savings Bonds

-- Where to Stash Your Cash

--Long-term Care - US government web site

-- Long term care conundrum

--Financial documents: What to shred, what to keep

-- Estate Planning: the Documents You Need

Thanks to everyone who participated and to Mark, the BEST producer in the world. If you have a financial question, there are lots of ways to contact us:

Call 855-411-JILL and we'll schedule time to get you on the show LIVE

Send an email: askjill@moneywatch.com

Tweet me: @jillonmoney

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    View all articles by Jill Schlesinger on CBS MoneyWatch »
    Jill Schlesinger, CFP®, is the Emmy-nominated, Business Analyst for CBS News. She covers the economy, markets, investing and anything else with a dollar sign on TV, radio (including her nationally syndicated radio show), the web and her blog, "Jill on Money." Prior to her second career at CBS, Jill spent 14 years as the co-owner and Chief Investment Officer for an independent investment advisory firm. She began her career as a self-employed options trader on the Commodities Exchange of New York, following her graduation from Brown University.