Dear Helaine: My wife has been accepted into law school. It’s a private university -- a fancy, highly ranked one that costs a lot. A lot! I’m in my 40s and she’s in her mid-30s. We have investment savings, and our IRAs are on par with what is expected of folks gearing up to retire in their early 60s. We also just sold our house in San Francisco, which left us with a tidy nest egg -- enough to pay for her to attend the school, with a chunk of change left over.

My question: What should we do in terms of taking out loans vs. spending our savings? My wife wants to use her law degree for political advocacy work for the underdog, so it’s not likely we’ll have a high salary from her degree. While she is in school, my salary will support both of us, but not leave much to contribute to any kind of savings. Do we take out loans, ones that will accumulate interest while she’s studying? Or do we spend our cash on her schooling? -- Legal Loans or Savings

Dear Legal Loans or Savings: There’s a lot to unravel in this deceptively simple letter. A “fancy” law school that costs “a lot” is not necessarily synonymous with quality or future job placement outcomes. I would urge both of you, if you have not already done so, to look at law school job placement stats and determine how many people graduate with a law job in hand, or obtain one shortly after graduation, and how many of those people work in the non-profit or advocacy sector in some way. Is there a less-expensive public university that would offer an equivalent or better outcome?

But let’s say the school passes all these questions with flying colors. My advice: Use the cash set aside to pay for law school, and don’t take out loans if you can help it. This will give the two of you the most financial freedom in the long run. Many people say they want to work for the non-profit sector, but find their loan payments so fiscally constraining, they end up taking higher-paying positions (read: corporate law) they don’t really want to pursue, simply because they need the larger salary to pay their student loan tab. Do you really want to put your wife in that position?

At the same time, there is nothing stopping your wife from getting a direct, unsubsidized loan from the federal government if your family circumstances change in the future -- say, you lose the job that’s supporting the family while she’s in law school. One thing I wouldn’t factor in to the decision: public service debt forgiveness offered by the government. It’s not simply that it’s not working as intended, and few recipients are receiving the forgiveness they were led to expect -- a scandal in itself. It’s that plans change, and if your wife decides she ultimately doesn’t want to do advocacy for a non-profit, she won’t receive the debt forgiveness.

(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’m writing with a question about medical expenses in retirement. Over and over, I keep reading something to the effect that “a couple retiring today can expect to spend $250,000 on medical expenses during their retirement, even with Medicare.” I realize Medicare doesn’t cover everything, but this seems like an unbelievably high number. Can you tell me where this figure comes from? Is it assuming some form of long-term care will be necessary? I am in my mid-40s and would like to know more about what those expenses are and how to plan. -- Young and Healthy Now

Dear Young and Healthy Now: The information you are thinking of almost certainly comes from Fidelity Investments, which releases an annual study attempting to estimate the medical expenses of a theoretical 65-year-old couple retiring in the current year. They released the most recent one this past April, and the number is $285,000 -- worse than you think. Women can expect to spend $150,000, while men spend a slightly lower $135,000. It’s possible these numbers are low -- they do not count such things as dental expenses or long-term care. HealthView Services, which also performs an estimate and includes these things as well as other costs not covered by Medicare, puts the number at $387,644 in today’s dollars.

Now of course Fidelity has a reason for wanting you to know that number: The press release trumpeting their finding also contains a pitch for Fidelity’s Health Savings Accounts, which you can use if you have a high-deductible health insurance plan. The money is contributed and grows on a pre-tax basis and there are also no taxes due if the money is withdrawn and used to pay medical bills. And this is indeed one way to plan. If you are saving the recommended amount for retirement, and you can afford to still put more money aside, you might want to put $3,500 -- the maximum an individual can contribute -- in an HSA. (Families are permitted $7,000.)

But the bigger question is: Why is the amount we will spend on doctors and hospitals and other medical needs in retirement so high? Americans pay significantly more for their health care than any other nation. Medicare -- despite what many think -- does not pay for everything. It comes with co-pays and a host of gotchas -- for instance, if a hospital doesn’t formally admit a Medicare patient, and keeps them on “observation” status, the program won’t pay for a stay at a rehab facility, even if it’s needed.

Yes, it’s good to save. But no other first world nation imposes this sort of burden on its residents. Fixing that would be the best savings plan of all.

(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 house is in a booming neighborhood in an "it" city. I only have a $50,000 mortgage. The property would appraise for about $300,000. It's a large lot, with a house and detached garage in so-so condition. It needs some work.

I would like to buttress my retirement savings, and I have two ideas of what I can do. I could subdivide it, and then sell the lot for a pretty penny. I would lose my garage and most of my yard, but I would have a chunk of change in the bank, which I could invest in my retirement.

Or I could tear down the detached garage and build a new one with a granny flat apartment to rent above it. I could then do a traditional rental or Airbnb. (I'm leaning toward the traditional rental.) A friend of mine recently did something similar and, based on her experience, I speculate this would cost me about $125,000. Based on what rents are where I live, I believe I could rent the apartment for enough to cover the increased mortgage payment and other costs. What do you think? -- Home for Good

Dear Home for Good: The personal finance community likes to promote earning money as a landlord as "passive income," but it's frequently anything but. Tenants can call in the middle of the night, short-term guests can be wonderfully charming or a difficult handful. Either way, the person living in your property will be a most definite presence in your life. Expenses are often somewhat more than you expect -- you are now maintaining two properties, not one. You've doubled the number of sinks and roofs that can spring leaks.

That's not to say selling the land is an ideal situation either. It will cost you money in the long run -- homes lacking a detached garage or decent yard space do sell for less than those with them. You will, moreover, be living next to a construction site, and you'll ultimately have a neighbor you have no control in choosing living very close to your home. A difficult tenant is a relatively temporary problem, but you'll live next door to a problematic neighbor for a much longer period of time.

If you still want to go ahead after weighing all these pros and cons, I suggest sitting down separately with both a real estate attorney and an accountant. You want to know the laws regulating both short- and long-term rentals in your neck of the woods, and then you'll also want to run the numbers with someone knowledgeable, objective and neutral. You need to know whether you have a financial cushion for contingencies ranging from the inability to rent the property out at the price you need to paying for unexpected repairs. If we want something, it's easy to underestimate the potential expenses and make the numbers work in our head. It's harder to fool a professional.

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

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