There comes a point when worry about a family's financial security does a generational flip-flop, with children fearing for their parents' well-being. While it's tempting to keep conversations with your parents or older relatives limited to the weather and the latest family gossip, talking to them about their finances can help ease your mind and give you a head start on mulling over what you'll face in the future.

Below is a roundup of the biggest financial issues senior Americans face. To help your parents polish their golden years to a high shine, use the tips and tools below and tackle the challenges as a team.

Income-stream agitation
Mom and Dad's finances may have seemed fine last year, but after the market's recent haircut, can their portfolio keep up with their current lifestyle for years to come? Hopefully they kept the cash they need for living expenses for the next five years out of the stock market. If not, then it's time to have a heart-to-heart about asset allocation.

Once their near-term spending money is squared away, you want to make sure your folks aren't overpaying for their investments. The same way that fees have a severe effect on your savings, they also hamper your parents' spending power.

Consider the example of a retired married couple withdrawing $40,000 a year from a $1 million portfolio of mutual funds that charge annual expense ratios of 1.5%. During the first year, they'd cough up $15,000 in fees. If they had invested in a low-fee fund with a 0.18% expense ratio instead, they would have cut their annual tab to just $1,800 -- and kept an extra $13,200 invested. What's more, over one year, earning 10%, that $13,200 would itself have generated another $1,320 in gains -- merely on the money they refused to surrender to the overpaid suits on Wall Street.

Help Mom and Dad assess their fees with FINRA's Mutual Fund Expense Analyzer. To measure the probability that their assets will sustain them throughout retirement, check out T. Rowe Price's Retirement Income Calculator.

Social Security insecurity
Seniors might not have to worry about Social Security running dry (studies estimate we have until 2037 before it's tapped out), but that doesn't mean they can rely on it for much support. The average annual Social Security benefit is roughly $12,500. Given that most retirees need much more income, pensions or retirement plans and personal savings have to cover the rest.

But problems can arise when these benefits are lower than expected, either due to taxes or because you retire early. With many people stopping work earlier than expected due to health problems, layoffs, or having to care for loved ones, a shorter pay history can make your benefits suffer. Keep this in mind if your parents have yet to retire, so they don't cut their earning and savings years short.

To wring as much as they can from their benefits, your parents need to keep close tabs on how that money is taxed. Careful review can make the difference between paying no income taxes on Social Security and paying taxes on up to 85% of it. Minimizing the IRS's take can translate into more after-tax income for them.

A good tax advisor can stretch those dollars and keep more for your parents and less in the IRS's coffers. The Social Security website also has a number of tools and FAQs to help with planning. Check out its screening tool to see if your loved ones may be eligible for other assistance offered through the Social Security Administration program.

Health-care cost concerns
It's an unavoidable fact of life: As you age, you spend more on health-related costs. And even when Medicare kicks in, your parents will still have to pick up a large portion of their medical tab with insurance and cash from their nest egg. Your parents could easily need $250,000 to $500,000 to cover health expenses in retirement -- and that's assuming Medicare benefits remain at current levels. Suddenly a smoothie maker and set of free weights don't seem like such a bad stay-healthy gift.

Log on to the Medicare website to help your parents get the most from their coverage. See what preventive services are offered and use the coverage database to see how much they'll pay for services and supplies for ongoing health issues.

Help your parents cut drug costs as well by purchasing through online pharmacies. Order only from sites with the Verified Internet Pharmacy Practice Sites (VIPPS) seal of approval. If your parents don't have good drug coverage, check pparx.org for patient-assistance programs.

Taxing matters
Spoiling the grandkids is one thing. Being overly generous with Uncle Sam is simply uncalled for. When your parents begin tapping into their retirement accounts, they can keep tax bills low by drawing from taxable accounts first and letting tax-deferred accounts (like IRAs and 401(k)s) continue to grow. Pull from Roth IRA savings last.

Taking advantage of senior-citizen tax breaks is key. If your parents don't itemize, make sure they're getting the increased standard deduction. At the state level, look into perks such as breaks on property taxes and IRA or annuity withdrawals.

On the deductions side, it pays to keep good records. Medical costs can easily amount to more than 7.5% of their adjusted gross income, allowing them to deduct the expenses that exceed the 7.5% threshold. If that occurs, look for other expenses to write off (e.g., installing handicapped access at home). Additionally, a portion of what they pay in health- and long-term care insurance premiums may be deductible.

If your parents' income is low enough, and you provide 50% or more of their support, look into claiming them as dependents. Doing so allows you to give them a hand with medical expenses and add those deductions to your own tax return (as long as you pay the provider directly, not your parents; otherwise, it's considered a gift). To navigate the tax code, find a good tax planner (see "Find a Tax Pro in the Know" for tips on finding a keeper).

For more Foolishness:

Dayana Yochimpracticed her heart-to-heart on the dog before trying it out on her parents. She has been schooled by the Fool's disclosurepolicy.