Dear Helaine: I’m in my mid-50s, and I left the workforce (where I made low six figures and socked away money) to move back to a city I left decades ago and back to my parents’ home to take care of them. They are both in their early 80s and ill with neurological diseases that rob you of movement or mind, but don’t actually cause death. Both need more and more help, and it’s expensive. They have no long-term-care insurance; it’ll all be out of pocket.

They have a net worth of about $2 million and receive about $12,000 a month from a pension, Social Security and required distributions. I’m trying to figure out how to best invest their money (I have power of attorney) to cover their increasing medical costs, yet also leave me and my sibling (he lives in Europe and gets half of what’s left) something to somewhat make up for the cost of leaving the workforce to care for them full time.

Family values have always been that we earn our own way, so their view is that “we can spend it all.” Technically, I support that, but I really supported that before I had to leave the workforce and stop making my own money and contributing to my own Social Security and savings. What’s your advice? -- Dutiful Daughter

Dear Dutiful Daughter: I reached out to Carolyn McClanahan, a certified financial planner specializing in medical expenses and issues, on your behalf. She and I agree. The first thing you need to settle is what you are going to get paid in return for giving up a six-figure job to take care of mom and dad.

If you make this a formal arrangement, you can get paid market rate, still continue to contribute to Social Security, and your parents can deduct it as a medical expense on their taxes. I also think it would be beyond fair if you received some additional compensation in their will as well, especially since your sibling is leaving all this caretaking to you.

If your mom and dad won’t do all that, you need to seriously re-evaluate returning to your professional career. It’s one thing to teach a child to earn her own way, but it’s not fair to prevent her from doing so. One thing you do not need to worry about: If your parents have an income of $12,000 a month, combined with their substantial assets, they will likely be able to afford both assisted living and live-in aides. You don’t need to sacrifice your financial future, not to mention your personal and professional lives, to make sure they are taken care of adequately.

As for investments, I would attempt to calculate what your parents' cash needs will be going forward before coming up with an investment plan. It’s quite possible they will need to move into assisted living or even a nursing home at some point in the future, and money will need to be available for that. There is only so much a middle-aged daughter can or should be expected to do.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Dear Helaine: I like to be generous. A friend and I went to dinner at a restaurant at my recommendation. I tried to pay for our dinner with some gift cards I had. She tried to make me use them only on myself. She spoiled my enjoyment of our dinner. Why couldn’t she just enjoy the dinner and the fact that I wanted to use my gift cards on her? -- Generous Pal

Dear Generous Pal: You mean well, you really do. You wanted to go to a particular restaurant, and you wanted a friend to join you. You wanted to use a gift card, and you absolutely did right to offer to cover the cost of the meal. Personally, I think it’s a bit tacky to use a gift certificate to pay for your share of the bill for a meal and not make that gesture. Clearly, you agree with me!

However, here’s what you can’t do: You can’t force anyone to accept your generosity. No matter how much you wanted to pay the bill, no matter if the person you were dining with could use a bit of financial help, there’s no way. We can’t control other people. As long as you tried to do the right thing, I don’t think you should have allowed it to impact your enjoyment of the meal and time with your friend.

In the future, I would suggest explaining in advance that you have a gift card and would like to use it to cover the both of you. This way, you aren’t putting anyone on the spot, and you can enjoy the meal however you both pay for it.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Hi Helaine: I’m 25 years old and have around $50,000 in student loan debt from undergraduate and graduate school. My mother recently passed away, and I’m inheriting about half a million dollars in various forms of assets. There are liquid assets, some real estate and an annuity. Should I leverage part of this inheritance to pay off my student loan debt in full?

I’m tempted, but have three reasons I’m hesitant to do so. What if Congress passes retroactive student loan forgiveness legislation? Or would I be better off keeping my inheritance in its current form? What are the tax consequences of selling? Finally, my hope is that this inheritance sets me up for retirement. Let me know what you think! -- What to Do?

Dear What to Do: First, let me say I’m terribly sorry to hear about your mother’s passing. I’m sure this is a difficult time for you and your family, and I would urge you to be good to yourself and not rush into any decisions. But here is one thing you don’t need to worry about: The odds of Congress passing retroactive student loan relief are less than zero, sad to report. At the moment, the U.S. government can’t even bother to ensure that borrowers promised relief via the public service loan forgiveness program receive it.

So that begs the question of what to do next. I am all but certain you’ll be rejiggering this portfolio to reflect both your age and risk tolerance. I see no reason why you can’t take some of the funds and pay off the student loans early while you are at it. The question is how to do it. What kind of penalty will you pay if you sell the annuity? Are you planning to live in the real estate you inherited, or do you hope to rent it out? If the latter, are you up for being a landlord, or is the income you generate going to be more trouble than it’s worth?

Finally, you will need to pay capital gains taxes for any uptick in value of the investments you sell from the time your mom died to when the property or investment is no longer yours. I’d suggest sitting down with a certified financial planner, working out the numbers, and taking it from there.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)