Jill on Money: Dow record high, tax planning

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Here's a coincidence: In a week where the Dow Jones Industrial Average saw four consecutive days of record nominal closing levels, it's also the four-year anniversary of the recent stock market low! On March 9 2009, this is where the indexes closed:

  • DJIA: 6,547 (lowest point since 4/15/97)
  • S&P 500: 676 (lowest point since 9/12/96)
  • NASDAQ: 1,268 (lowest point since 10/9/02)

Since then, all three indexes have more than doubled; the Dow has reclaimed it's all-time high (though to reach the inflation adjusted level, the Dow would have to climb to 15,731.54); and the S&P 500 closed within 14 points or 1 percent of its October, 2007 all time high of 1565. All of that is interesting news, but our callers had other, more pressing issues than the value of a stock index.

Maria from OH is concerned that too much of her retirement savings is pre-tax, while Jen in RI and Deanna in Seattle are trying to balance out their low risk tolerance, while understanding that shunning the equity asset class may not be the best strategy.

Seth and his wife are considering a purchase of long term care insurance, but they are trying to figure out when it might be most affordable. Elise is also weighing LTC, but is more concerned about the cost of her health care between retirement and Medicare. KDC wants to know when to claim Social Security benefits - the answer might surprise you!

With just five weeks to go before tax filing deadline, we were fortunate to have CPA Peggy Murphy of Hungerford, Aldrin, Nichols & Carter, PC in Grand Rapids, MI join us as a guest. Peggy is the rare CPA who can actually speak English - of course our friends at WOOD Radio totally hooked us up!

Peggy highlighted these often-overlooked deductions for individual taxpayers:

- Long term care insurance premiums

- Investment advisory fees

- Certain legal fees

- Tax prep fees or software

Here are Peggy's tips for small business owners:

- Determine whether charitable donations could be marketing expenses

- Ensure that you are claiming your rightful depreciation

- Open a retirement plan that matches your needs

While we had her on the air, Peggy also answered a question from Kevin, who asked about his ability to use a 401 (k), a 457 and a solo 401 (k) or SEP.

Randy from Louisville, KY is wondering what to do with proceeds of his house sale...with 4 daughters, we spend the money quickly!

David, a 34-year old orthodontist is making a lot of money, which is good since he has $110K worth of student loans. His dilemma is whether to pay down the loans or preserve his cash to open up his own practice.

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

-- The ABCs of Annuities: 6 Questions to Ask

-- The Pros and Cons of Annuities

--Immediate Annuity Calculator

-- Annuity salespeople don't like me

-- Social Security: Manage your account online

-- Social Security estimator

-- When to take Social Security?

--Social Security: File and Suspend

-- Social Security: Double-Dipping

-- Medigap insurance

-- Retirement Calculator

-- Retirement Plan Required Distribution Calculator

-- Long-term Care - US government web site

-- Long term care conundrum

-- Life Expectancy Calculator

-- Life Insurance calculator

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

-- Estate Planning: the Documents You Need

-- NYT Rent vs. Buy Calculator

-- Re-Fi Calculator

-- Another Re-Fi Calculator

-- Reverse mortgage info via HUD

-- Reverse Mortgages: Don't let the Fonz sell you

-- 529 plan info

-- College Loans: What you need to know

-- Student Loan Consolidation

-- Money As You Grow

-- National Foundation for Credit Counseling

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@jillonmoney.com

Tweet me: @jillonmoney

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    Jill Schlesinger, CFP®, is the Editor-at-Large for CBS MoneyWatch. She covers the economy, markets, investing or anything else with a dollar sign. Prior to the launch of MoneyWatch in 2009, Jill was the chief investment officer for an independent investment advisory firm. In her infancy, she was an options trader on the Commodities Exchange of New York.

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