Our advice columnists have heard it all over the years—so we’re diving into the Pay Dirt archives to share classic letters with our readers. Submit your own questions about money here. (It’s anonymous!) 

Dear Pay Dirt,

My friends and I are early 30s professionals living in one of America’s most expensive cities and making middle-class incomes. None of us can afford to buy or save for a home here. We all rent, but we’re not broke. We save for kids and retirement and illness, but a home isn’t in the cards. But recently, we think we might have found an unconventional loophole.

Four friends and I have been considering buying a vacation home a few hours away together in a cheaper rural area. There’s a long distance between “considering” and “doing,” but I do my due diligence about purchases. What are the key things to consider in an arrangement like this besides 1) stability of the friendship 2) ongoing ability to meet the financial commitment 3) getting everything (maintenance, taxes, ground rules, etc.) in writing? I’m genuinely interested in trying this when the market cools in a few years, and I want to think through the financial mechanics first.

—Togetherness in 2025

Dear Togetherness,

I love the idea of buying a vacation home with friends, but I do agree you need to do your due diligence before getting started. A lot goes into buying a home and doing it with others, even if they’re close friends members, adds a whole extra value for caution.

Discuss who will all be on the mortgage and if their credit will allow them to qualify for the mortgage itself. There’s technically no legal limit on how many people can be on a mortgage, but typically four people is the max on most. However, some lenders will consider more since there are five of you. Your finances will be reviewed, looking for criteria such as income, credit scores, current debt, and employment. So, if your friends have a less than subpar credit score, or lack in these areas, they’ll need to work on it over the next few years.

Note that a joint mortgage does not mean joint ownership. Make sure everyone’s name is on the title and deed, so there is no confusion about who owns the house. You might also want to consider what kind of shared ownership agreement you want. Joint tenancy allows everyone to have an equal share of the house and is strict about the right of survivorship—if one of you dies your share is passed on to the remaining parties—and financial responsibility. Meanwhile, in an agreement like tenancy in common, if one of you should pass away, your share is left to your heirs and may need to go through probate.

I’d also speak to a real estate attorney. Different laws in every state discuss how property should be divided in case one of you can no longer keep the financial commitment. You’ll want to make sure everything is as straightforward as possible so there is no confusion as to how things will work so your friendship won’t be damaged.

—Athena Valentine

From: My Brother Says I’m Not “Allowed” To Have Kids Because I Have To Care For His. (August 26th, 2022).

Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.

Dear Pay Dirt,

My husband and I are trying to figure out how to be fair to our two sons regarding their inheritance. We each have one son from a previous marriage. We only have one asset which is our home. We were very fortunate to buy at exactly the right time and our home has doubled in price. My son and grandson moved in with us when we bought the home. He is 48 years old and my grandson is 30. He and my grandson pay half the mortgage every month. My son makes repairs around the house and yard. He and my grandson buy groceries, make car repairs, and help with utilities.

My husband’s son, who is 30 years old, lives in another state with his girlfriend. They are buying their own home together with the help of her mother. My son and grandson love our little town and house. They want to stay here. They have limited resources and we live on social security so we are all able to survive together with our combined resources.

Basically, the house will be left to the two sons. If my son and grandson are forced to sell the home to give my husband’s son his fair share they will most likely not be able to buy a new home as the new market will have priced them out. So, my husband’s son will have his own home and my son and grandson will be forced to sell and leave our home and no longer have a home of their own. They have invested heavily in this house and us. They will not have the means to buy their stepbrother out. We know there must be a way to do this fairly but we get emotional and lose perspective. We would love some advice on possible options.

—There Must Be a Fair Way to Do This

Dear Must Be A Fair Way,

This is a difficult situation and I can see why you’re struggling to figure out what’s right. You want to make sure one kid is taken care of while ensuring the other kid doesn’t feel like you’re punishing them for being successful in life. But in this situation, I would say leave the house to your son. Your son has not only helped pay half of your mortgage for years, but he has also contributed to the utilities, and the cost of repairs done to the property—not to mention has even fixed them himself.

Talk to an estate attorney to create a trust that would allow your son to be left the home. If he chooses not to keep the home, and sell at a later time, set it up so that any proceeds from the house will be split between him and your stepson. This way if he chooses not to keep the family home, or can’t afford to, both sons are included.

I would also think about how you plan to broach this conversation with your stepson. It might be helpful to talk it through with a therapist beforehand. In a lot of families, one child who isn’t as financially well off as another sibling will inherit more of the estate than the other one, which causes resentment. You want to be as levelheaded as possible so the conversation doesn’t get emotional ad if it does, you’ll be able to rein it back in before it gets out of hand. Try to make sure your conversation with your husband’s son is a healthy one that leaves both of you feeling at ease with the decision.

—A.V.

From: I’ve Found A Trick To Buy My First House. But I’m Worried It’s Super Unethical. (August 3rd, 2022).

Kristin Wong
I Want to Teach My Kids One Final Lesson From Beyond the Grave. Trust Me, They Deserve It.
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Dear Pay Dirt,

My husband and I rent the same cabin for a week each year. My sister has said she would like to come up with us next year. We’re fine with this; we travel well together and she’s come with us in the past. Next year, however, her new husband will join us, and although we enjoy him well enough, he’s a huge cheapskate. For example, they come over or we go out for meals multiple times a month together. We treat often, and although my sister will treat us back occasionally, he has given us money exactly twice in three years of this.

The cabin we rent has enough space for them, so it won’t cost us any more to host them. We also rent a small boat for the week we are there; we would rent it either way. I know my sister would never rent one on her own but she will certainly go on the boat whenever we take it out.

My question is: Do I ask them to pay anything for the cabin (or the boat)? Our husbands make about the same money; she makes half of what I do but we both make good salaries so financially it’s not a stretch for any of us. I’m inclined to ask for a portion toward the cabin given that she invited herself, but I can’t tell if I’m just being cheap in response to her husband’s historical cheapness. Help!

—All I Want Is a Stress-Free Vacation

Dear All I Want Is a Stress-Free Vacation,

I think if you haven’t asked your sister to cover part of the costs in the past, it may be a little awkward to ask for it now. It seems like you mostly just want her cheap husband to start paying his share, which means paying his portion of any other expenses you’d incur outside of what you’d normally spend anyway.

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Either way, this is why God made Venmo. Tell your sister ahead of time that you’d like to handle splitting expenses via Venmo (or another app that allows you to request payment, like Zelle or Cash App), and then she and her husband know to expect that they will need to cover some of their own expenses. Then you can send them a request for whatever they owe, and you won’t be leaving it to them to estimate (or in her husband’s case, underestimate) their portion. Splitting food, drinks, and money for any excursions you might take are reasonable requests.

I would not assume, however, that this teaches your brother-in-law anything about being cheap, and being cheap in response will not do that, either. It is reasonable to ask them to cover some of the costs of the trip, though. If the costs don’t really matter to you, you may be risking some tension with your sister, just to retaliate against her husband’s cheapness, and I doubt that’s worth the money. So while it’s not wrong to ask them to cover their share, you should think about your own motivations and what you believe the outcome will be.

—Elizabeth Spiers

From: My Co-Worker Is Getting Seriously Underpaid. Do I Tell Her? (August 4th, 2022).

More Money Advice From Slate

I have a friend who’s always been a little cheap with shared checks. If I throw my card down for ease and let people Venmo me, he’ll pay me, like, a conservative estimate of his portion (often short of the real total) and also not take tax or tip into account. I always kind of forget about this until he does it again. A few months ago, he estimated $25 when he owed me $40, and I was like, “Bro,” and he seemed perplexed and gave me the $40. I tell you all this because on our last hangout, it was just us, he reluctantly revealed he is an heir to one of the biggest family fortunes in America.

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