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)

Dear Helaine: My husband and I own a home and have put two children through college. We carry financial debt for that, but we have frozen payments for a while.

My 10-year-old business has taken a nosedive, and I lost money last year. I am looking for a job, but there are not many companies wanting to hire a 60-year-old woman. In addition, we’ve needed to support my husband’s parents. As a result of all this, we have $75,000 in debt.

Our house is worth just under $900,000. We can’t refinance because I didn’t earn income last year. We’ve been trying to sell it for a few months, but we’ve received no firm offers. We owe $575,000 on it. I really don’t want to declare bankruptcy. What do you suggest? -- Desperate but Not Underwater

Dear Desperate: Take a deep breath. You need to think long and hard about your current reality. The deus ex machina of a one-time financial windfall is not a long-term solve.

While it seems like your business collapse is the cause of your financial woes, in fact, you and your husband have been living at the financial edge for a long time. It seems obvious in retrospect you couldn’t afford to support your in-laws, nor could you afford all the college loans you took on.

My advice: Meeting with a bankruptcy attorney is not the same as committing to filing for bankruptcy. So do it. Also sit down with a debt counselor. You need to slowly but surely examine and weigh your options.

I’m not convinced selling the home is the right step. Where do you plan to live afterward? Can you afford to rent where you are now? Or will you ultimately need to move to a cheaper geographic region, putting your husband’s earnings in jeopardy?

And, since this is your only asset, what are you planning to tap into at retirement? Will you really invest the funds you net from selling the home and paying down your debt, or will you slowly but surely spend the money in yet another attempt to keep up with what you think you should do? I can also all but guarantee you will not net as much from this home as you think, for the obvious reason that if it was worth what you think it is, it likely would have sold by now.

One other thing: It’s easy to say you’ll work till you drop, but you are learning a hard lesson right now -- many people are forced out of the workforce early due to events beyond their control. As a result, you need to make a plan.

(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: My financial life feels extremely unbalanced, and I don’t know where to begin to fix it. Thanks to a divorce settlement many years ago, I bought a house in a popular summer community. It’s now worth $2 million, and I own it free and clear. My finances worked as long as my ex paid child support, but our daughter aged out of it, and I am slowly sinking in a very expensive boat.

I have $30,000 in debt, and I haven’t filed taxes in a few years. I work for myself, and while I earn enough to get by and maintain the home, I have no retirement accounts, no health insurance, and no ability to get a mortgage so I can take money out of the home. The older I get, the more challenging this all starts to feel.

I met a couple of older gentlemen, clearly successful and now retired, through a local program to help small business owners. Both suggested I sell the house, use about $1 million to buy a new, less-expensive one somewhere nearby where I can rent rooms out via Airbnb, and put $500,000 in an annuity for a guaranteed income. Everyone I ask hates the annuity idea, but how else can I stabilize my income? -- House Rich and Cash Poor

Dear House Rich and Cash Poor: There is only one way to move forward. That’s one step at a time. So where to begin?

You are going to have a very hard time getting your financial life organized as long as those taxes aren’t filed, so I would suggest calling an accountant as soon as you read this note and getting on the process of filing the taxes. The IRS will likely work out a payment plan with you, so you won’t need to come up with a lump sum for all the back taxes and penalties at once.

Second, you need to hope your health remains good and you suffer no accidents till the next Affordable Care Act insurance open enrollment period. As it stands right now, if something goes wrong, you could owe a lot of money to various hospitals and doctors.

As for the home -- where the tax money will come from and likely your retirement savings, too -- sell it. Don’t buy another large house. Purchase a small condo that you can afford and invest the difference. Airbnb is not a guaranteed income stream.

Next, all your friends are right: Don’t listen to random men who give you investment advice. An annuity is an extremely complicated, high-cost investment, one that locks up your money for a long period of time (sometimes permanently). The reason it gets pitched is because the people selling annuities make major commission money peddling them.

When you are ready, sit down with a financial adviser working to the fiduciary standard and come up with a plan. And while you are doing all this, work out how much you need to live on and not run up debt.

I know this is all tough, but it will get easier as you go on. The paralysis is part of the financial problem. As you push back on it, the pressure on you should release.

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

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