I have a confession: Before I began writing this column, I thought a good college-savings plan was to set aside some money each month for my son’s “529” account. But after just a few months of seeing reader questions and tracking down answers, I’ve come to realize that the save-and-forget mentality doesn’t begin to deal with the host of challenges faced by any parent or grandparent hoping to contribute toward a child’s college education.

In particular, all sorts of decisions we make long before college begins—or even before a child is born—can affect aid eligibility, taxes and more.

This month, we have once again tapped experts for their advice and insights to help readers understand these challenges. Read on for experts’ answers.

To help my grandchild with college costs, I am planning to transfer $5,000 a year directly into his bank account just before school starts to avoid affecting his financial-aid and scholarship package. Is this a viable plan?

No, not in the way you hope.

While such generosity wouldn’t have an effect on the student’s first year of school because the Free Application for Federal Student Aid uses the prior year’s income in its formula, college-planning experts say it would have to be reported as income on subsequent years’ Fafsa forms and would affect the student’s expected financial contribution going forward.

The $5,000 given to a student must be reported on Fafsa as “money received or paid on student’s behalf,” according to P.J. Walsh, a certified financial planner who runs his own firm in Chicago. “The first $5,000 would not have an effect on his first year of school,” Mr. Walsh says, “but would have to be reported as income on the next year’s Fafsa form, affecting his expected contribution for his second year of college.”

However, experts note there is a sort of backdoor option to contribute to a student in his or her graduation year. “You could wait to help pay for your grandson’s tuition until the Betlike second semester of his junior year, after he’s already filed his last Fafsa,” says Joe Hurley, a certified public accountant and founder of savingforcollege.com in Pittsford, N.Y.

I have 25 Series E U.S. savings bonds that no longer gain interest. Would it be a tax write-off to use them to pay tuition for my grandchildren directly to a qualified institution?

Sorry, that isn’t possible in this scenario because they don’t qualify for the Internal Revenue Service’s education savings-bond program. That program allows a tax exemption on some or all of a savings bond’s interest, but there are many guidelines and restrictions:

• The exemption is applicable only on Series EE bonds issued after 1989 or Series I bonds, and the bonds must be in your name or the name of you and your spouse. And the bonds’ owner must have been at least 24 years old before the bond’s issue date.

• Redeemed funds must be used to pay qualified higher-education expenses for yourself, your spouse or a dependent you claim as an exemption on your tax return. And the qualified expenses don’t include expenses for room and board or courses that aren’t part of a degree- or certificate-granting program.

• Your modified adjusted gross income, or MAGI, must be “less than the amount specified for your filing status,” the IRS says in its parlance. Or, plainly said, if you make too much money, you’ll have to pay taxes on otherwise eligible savings bonds.

According to Mr. Hurley, for 2015 “the tax exclusion is phased out for individuals with a MAGI between $77,200 and $92,200, or $115,750 and $145,750 for married couples filing jointly.” The IRS also says your filing status can’t be married filing separately to qualify.

“Since these are series E bonds…they would not be eligible for this exclusion, and even if they were EE or I bonds, you would also be excluded based on the immediate-family stipulation,” Mr. Walsh says.

Readers who would like to explore the Education Savings Bond Program in greater detail should review IRS Publication 970, Tax Benefits for Education.

Mr. Hershberg is a Wall Street Journal news editor in New York. Email him at brian.hershberg@wsj.com.

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