A 401(k) versus an IRA: Which one wins this smackdown?

Dear Liz: I am a 27-year-old with a big investment question. The company I work for matches 401(k) contributions up to 9%, which is all well and fine since I contribute enough to receive the company match. I have just about $60,000 in my 401(k) and I have a Roth IRA on the side as well as a brokerage account for stocks. I would like to roll over my 401(k) into another IRA since the investment choices in the 401(k) are rather limited. I’m a big fan of investment diversification with different funds. Is this a good option to choose or is this a silly idea with no merit? I understand the tax implications involved but am willing to bite the bullet for more investment options.

Answer: Good for you for being so diligent about saving for retirement. Your early start should give you a lot of options when you’re older.

For now, your question has an easy answer. Typically, you can’t roll a 401(k) account into an IRA while you’re still working for the employer that provides the 401(k).

There are a few exceptions. Once you turn 59½, some plans do allow such rollovers. Also, a few plans offer “mega backdoor Roths” that allow you to contribute after-tax money to a 401(k) and then do an “in service” conversion to a Roth IRA. This option helps high-income people get around the income limitation that would otherwise prevent them from contributing to a Roth IRA.

You will have the option of rolling your money into an IRA once you leave your job, but don’t assume such a rollover is always the right choice.

Most 401(k)s offer enough options to give you plenty of diversification, plus you may have access to low-cost institutional funds that wouldn’t be available in an IRA. You’re also protected by federal law that requires the companies offering 401(k)s to act as fiduciaries — in other words, they must put your best interests first. You often have the option of rolling your 401(k) balance into a new employer’s plan, which means you would be able to take loans from the plan. That’s not an option with an IRA.

There are no tax implications for rolling over a 401(k), by the way. Only if you convert the money to a Roth IRA will you owe taxes. A conversion may make sense, but you’ll want to talk to a tax pro first.

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Protecting home sales proceeds from taxes

Dear Liz: My friend has been diagnosed with Alzheimer’s and is now living in a secure assisted living facility. After a year in this home, his sister finally sold his condo. Her tax person says he will take a big tax hit. I say it is totally medically ordered and he’ll need the money for his current housing ($5,000 a month) until he dies. I also question whether part of that $5,000 should be deductible because it is only ordered because of his illness. Your thoughts?

Answer: Your friend may not be able to protect all of his home sale proceeds from taxation, but he likely will be able to protect some.

If your friend lived in his condo for at least two of the previous five years before the sale, he will be able to avoid tax on up to $250,000 of home sale profits. Even if he fell short of the two-year mark, he likely would benefit from IRS rules that allow partial exemptions when the sale is due to “unforeseen circumstances.”

Meanwhile, medical expenses, including some long-term care expenses, are potentially deductible if they exceed 7.5% of someone’s adjusted gross income. Assisted living expenses may qualify as deductible medical expenses if the resident is considered chronically ill, which means they cannot perform at least two activities of daily living (eating, toileting, bathing, dressing, getting in and out of bed and remaining continent) or they require supervision because of cognitive impairment, such as Alzheimer’s disease or other forms of dementia. The personal care services must be provided according to a plan of care prescribed by a licensed healthcare provider. Typically, assisted living facilities prepare such care plans for their residents.

Liz Weston, certified financial planner, is a personal finance columnist for NerdWallet. Questions may be sent to her at 3940 Laurel Canyon, No. 238, Studio City, CA 91604, or by using the “Contact” form at asklizweston.com.