After retiring from their middle management jobs with a health insurance firm, a Colorado couple had one aspiration topping their bucket list. They wished to acquire a second home in downtown Chicago, the city where they grew up.

“They wanted to live in a spectacular condo with breathtaking views of Lake Michigan and Millennium Park, a super-popular urban space with multiple art venues. This was their passion and dream,” says Rich Harty, the real estate broker representing the pair.

Harty found them just what they were seeking: a three-bedroom apartment atop the Legacy, a 72-story skyscraper within the famed Chicago Loop. There they chose a $1.1 million unit with a professional kitchen featuring huge windows.

“The deal almost fell through, until they saw those drop-dead gorgeous views from the kitchen,” Harty says.

Despite fulfilling their longtime quest for a place in Chicago, this couple insisted on retaining their big family house in Colorado. That’s because their grown children and grandkids still live nearby.

“It was only because they’d been savers who invested wisely through the years that they were able to consider purchasing an expensive second home,” Harty says.

Of course, relatively few seniors can afford ownership of two properties. Yet some who are affluent see the advantages of two-home housing in retirement.

“Retirees have more leisure time than younger people to benefit from the contrasting settings and climates afforded by dual-home ownership. Take the classic case of ‘snowbirds,’ who spend their winters in sunny Florida or Arizona and summers in cooler northern states,” says Mark Nash, the author of “1001 Tips For Buying and Selling a Home.”

But Nash cautions all seniors to think through the many implications of taking on ownership of a second home in their retirement years.

“Those who buy a second property with a fixed-rate mortgage know their principal and interest payments will stay constant for the life of the loan. But they also need to anticipate potential increases in utility expenses and insurance. Also, condo fees and homeownership charges can skyrocket,” he says.

Here are a few pointers for second home buyers:

-- Consider the upkeep burdens associated with two-home ownership.

Margie Casey, an experienced real estate broker based in the Florida Keys, says that wherever they choose to live, most retirees want low maintenance. Ideally, they like all exterior upkeep to be provided through a condo or homeowners’ association.

“People want the total freedom of ‘lock and leave’ homes,” Casey says.

Though they’re determined to retain their Colorado house, Harty’s clients had to face squarely the reality that their home has many deferred maintenance needs. Hence, they made sure they included these expenses into their housing budget.

-- Take note of the financial implications of your plan.

Casey reviewed numerous retirement communities on the website she founded: realestatescorecard.com. This helped her realize that any seniors considering two-home ownership should first discuss the financial implications with a professional adviser.

“A planner can help you calculate what you can afford and give you a second opinion on your plan,” she says.

Property taxes are also a big factor, especially if local jurisdictions are running budgetary shortfalls and may have to raise taxes.

“Once you investigate the taxes, you may decide to buy one state away from your grandchildren, assuming that lowers your cost of living,” Casey says.

-- Try to determine if condo living would suit you.

Michael Crowley, a Spokane, Washington, real estate broker, says buyers considering the purchase of a condo should exercise caution before making this choice.

“After living in a house for many years, residing in a condo is a monumental change,” says Crowley, who entered the real estate field in 1993.

To illustrate, he tells of a married couple he advised on the purchase of retirement property in Hawaii. The couple chose a condo development that seemed attractive. Before they concluded a purchase there, however, they rented a unit as a trial run.

“After a brief time renting, they realized they hated condo living. It felt way too crowded to them,” Crowley recalls.

Those contemplating a dual-home retirement plan should be doubly cautious about buying two condos at once.

“For Pete’s sake, don’t buy two condos if you’ve never ever tried living in an apartment. There’s too big a risk of disappointment,” Crowley says.

-- Review your transportation options before buying a second home.

Many a retiree has selected an ideal setting without taking into account airport access, which Casey considers a major mistake.

Relying on an out-of-the-way airport makes it harder to travel to distant locations for vacation or to see your children. It can also add to your air transportation bills, which are already rising steeply in the post-pandemic period.

“Try to live near an airport that’s a hub for one of the major carriers. That can save you a ton on air travel costs,” Casey says.

Another transportation factor to consider is proximity to major interstate roadways.

“Most retired people want to live within a two-hour drive of their grandchildren,” Casey says.

-- Lower your expectations for visits with your offspring.

Living near grandchildren is the No. 1 priority for many retirees. But Casey cautions those choosing a retirement habitat to be realistic about their expectations for how often they’ll see family, no matter how close they live.

“Your kids have busy lives. Sure, you can hope to see them often. But don’t focus your whole retirement lifestyle on seeing family. First and foremost, choose the lifestyle that works for you,” Casey says.

(To contact Ellen James Martin, email her at ellenjamesmartin@gmail.com.)

America’s home sellers are in a commanding position, and statistics underscore this reality.

The inventory of available homes is down 18% from a year ago, meaning less competition. Meanwhile, homes flew off the market 10 days faster than they did at the same time last year.

But that doesn't mean that sellers can put little effort into prepping their homes for sale.

“Even in the steamiest of hot markets, it’s foolish for most owners to sell without eliminating their boxy furniture and many of their numerous belongings,” says Mark Nash, the author of “1001 Tips For Buying and Selling a Home.”

Ellen Waugh, a professional organizer who’s worked with many home sellers, says buyers can’t picture themselves living in a property filled with countless personal items, including storage areas brimming with accumulations.

“Sellers should know that potential buyers who come through will open every single cabinet, drawer and closet door in their house,” says Waugh, whose organizing firm is called The Tidy Pig.

Unfortunately, there’s no secret to plowing through one’s possessions in an expeditious manner. But hiring a professional organizer can help ignite action among people prone to delaying tactics.

Virginia Barkley, a professional speaker and author of “ClutterBusting For Busy Women,” says many people who’ve lived in a home for an extended period feel overwhelmed at the thought of paring down their possessions.

“It makes a huge difference to get outside help with such a big undertaking,” she says.

Barkley, who previously worked in the deadline-oriented field of film and television production, says the key to a successful home streamlining project is to plan ahead and maintain a positive attitude.

“You have to set a drop-dead deadline for yourself. And every single day, you have to remind yourself of your vision for the future,” she says.

Here are a few pointers for sellers:

-- Acquire the simple equipment you’ll need for the job.

Martha Webb, a home-staging expert and author of “Dress Your House for Success,” says an efficient decluttering program starts with the right gear.

To temporarily store items you intend to take to your next property, you won’t need fancy storage containers. In most cases, cardboard boxes will suffice. But look for boxes of uniform size -- like the bankers boxes sold at office supply stores -- which will stack neatly.

Once you’ve packed your boxes, place them in a temporary storage unit. Alternatively -- if you don’t wish to pay for the rented storage unit -- you could stash the boxes in your garage.

“Buyers are more accepting of a garage filled with well-organized boxes than they would be if the boxes were kept in some other part of the house,” Webb says.

-- Limit yourself to one room at a time.

Webb says you’ll feel crazy if you go back and forth from room to room, trying to battle clutter on several fronts simultaneously. Instead, she counsels you to take on just one space at a time, starting with your master bedroom and clearing out closets in this room first.

“Having ample storage, including large closets, is a huge issue for contemporary buyers. That means you’ll want to remove as much as possible from these spaces. Once you’ve cleared out enough, you should be able to see the back wall of your closets,” she says.

-- Show sensitivity when decluttering your kids’ bedrooms.

Young children feel an understandable sense of alarm at the notion that many of their toys will be packed up and put away. They need reassurance that their prized toys will be available to them once your family’s move is complete.

How can you calm your children’s fears? Webb suggests you transform the process into a game.

“Tell the children they can choose a few special toys and books to keep in their rooms until the move occurs. Mention that they can use these items -- along with the ones you’re putting in boxes -- for a ‘toy party' in the new house,” she says.

-- Allow extra time and attention to your kitchen.

“Kitchen storage is a major selling point for any house. The last thing you want is for buyers to see a kitchen so crammed with items that they’ll think it lacks sufficient space for their own dishes and food,” she says.

After you’ve removed all the superfluous items from your kitchen storage areas, clean out the cabinets and replace only those pieces you absolutely need for everyday use. The rest -- like extra cupcake pans or holiday casserole dishes -- should be sold, given away or sent to storage.

-- Remove items that could hurt your sale.

“Never leave anything in plain sight that could detract attention from the positive attributes of your property,” Webb says.

For instance, she recommends you remove all prescription medications from the medicine cabinets in your bathrooms. Leaving them there not only invites theft (especially of prescription painkillers), but also raises buyer questions about the people living in the property.

“Remember that it’s nobody’s business what medications you take,” Webb says.

She also suggests you remove from your bookshelves any titles that seem to convey a strong opinion on any topic, such as a political book.

“The odds are good that some people will see that controversial book and disagree with its author or contents. They might even judge you harshly for owning the book and -- fair or not -- that could translate into problems for your sale,” Webb says.

(To contact Ellen James Martin, email her at ellenjamesmartin@gmail.com.)

Since last December, a couple in their early 40s have been struggling to move from a small urban townhouse to a bigger suburban place near a top-rated high school for their two teenagers. But months later, they’re still empty-handed.

“For one reason or another, all their offers on three houses have fallen through. They’re now exhausted by the process,” says Ashley Richardson, the real estate agent working with the pair.

The couple don’t blame Richardson for their real estate misadventures. Rather, they blame each other for botched tactics that caused them to lose three houses to rival bidders.

Richardson, who’s sold homes through the Long & Foster realty firm since 1993, says that in her experience, couples’ disputes over home-buying strategies are now more intense than ever. They bicker over where to search, what to buy and how much to spend. They also differ on the best coping strategies for the bidding wars that still occur in many cases.

The root of the problem, of course, is that a scarcity of supply continues to push up prices and reduce buying options for purchasers.

“When it comes to any given situation, buyers have very few good choices available to them,” Richardson says.

Current statistics tell the story on the supply/demand imbalance behind the present seller’s market, says Danielle Hale, the chief economist for Realtor.com, the home listing company.

“For those looking to buy, rising home prices and mortgage rates are creating affordability challenges across the board,” Hale says.

During 2021 alone, the median listing price for properties throughout the United States rose 14.2%. Rising prices remain a frustrating point of contention for home-buying couples.

An underlying issue cited repeatedly by economists is high demand for property among young adults of the millennial generation, people born between 1981 and 1996. Meanwhile, the country is not constructing enough replacement properties to meet the needs of newly forming households.

“There’s been a construction shortage of 5.8 million homes over the last decade,” Hale says.

Here are a few pointers for home-buying couples:

-- Abandon the notion that either partner has all the right answers.

Real estate agents often observe battles fought between spouses trying to agree on home selection. And often, amidst the bickering, they hear one partner assert that the other is mistaken in expressing his or her preferences.

“A lot of times, clients don’t realize how stubborn and self-righteous they can get,” says Mark Nash, a long-time broker and author of “1001 Tips for Buying and Selling a Home.”

Nash urges couples planning a purchase to go through a methodical process of setting priorities before they venture into house hunting.

“As a first step, each partner should sit down alone to draft a list of their own wishes in a home. Only then should they get together to create a joint list -- one that reflects the factors most valued by each person,” Nash says.

But what if both spouses are unclear about what they’re seeking in a home? One method of gaining focus is to “go negative.” List all the things you dislike about the place where you now live, then flip these to reveal what you want most.

For instance, suppose you abhor the noise and fumes associated with the traffic that rumbles through your neighborhood. Reverse that and see how important it is that you choose a home on a quiet, dead-end street or a cul-de-sac.

-- Seek an experienced agent to help iron out differences.

Some would-be purchasers, especially those planning to buy in high-cost areas, struggle to reach agreement on how best to allocate their scarce dollars. In such situations, each partner should focus not only on their priorities but also the trade-offs they could accept, says Merrill Ottwein, an experienced Coldwell Banker broker.

“Perhaps the wife thinks their top priority is getting a three-bedroom house with a room for each kid. But he’d rather have a two-bedroom house with a garage large enough for their SUV. When they can’t have both, their real estate agent can help them pick their better trade-off,” he says.

Of course, agents aren’t relationship counselors, and they can’t be expected to resolve irreconcilable differences between partners. But they can help mediate conversations that help couples settle minor disputes.

“A good agent will ask penetrating questions, encouraging the buyers to reach their own conclusions,” Ottwein says.

-- Give yourself ample home-shopping time if your marriage is young.

Obviously, people who’ve been married for many years know a lot more about each other than do those who began living together just a few weeks or months ago. Therefore, newlyweds will need to deliberate longer to ensure that both partners’ views are taken into account when a home is chosen.

“People who’ve just gotten remarried after many years of living alone should be extra wary about misjudging a partner. Your spouse may have developed some very strong predilections through the years,” Ottwein says.

You may need several long conversations, or perhaps even a getaway weekend, to reach agreement on the best housing choice for both of you.

“It’s a whole lot better to hash out your differences before picking a property than to make a choice your partner hates -- which could lead to major quarrels later,” he says.

(To contact Ellen James Martin, email her at ellenjamesmartin@gmail.com.)