Models of pre-retirement planning, Don and Reina Weiner bought an acre of land almost a decade ago in the Woodlands of Chapel Hill, a mixed-age community in North Carolina.

The couple, living in Leesburg, Va., at the time, had visited several towns around the country in their hunt to find a place to live when Mr. Weiner was ready to leave his job as senior sales director at Airbus Americas. Chapel Hill met their three criteria: warm weather, access to top medical care and proximity to a university to continue learning, Mrs. Weiner said.

So they paid $130,000 for a lot and $11,000 to an architect to design their dream home. They sold their townhouse in Leesburg and rented an apartment in Chapel Hill so they could supervise construction.

That’s when Mr. Weiner, now 68, and Mrs. Weiner, 67, hit a barricade. “I had a significant allergic reaction to the environment,” Mrs. Weiner said. She felt an intense pressure in her head. Her throat hurt. There was sinus pain. “The question was, Could I live here?” she said.

They decided to hold off breaking ground on the home while she tried to see if she could acclimate to the area. But she had an epiphany: “I decided you know what, this is crazy, I’m trying to do something that I can’t do.” So they regretfully put up the ‘for sale’ sign on the lot, and are back in the search for a place to live.

“The whole experience was disappointing,” Mrs. Weiner said. “There was money that just went flying out the door. On the other hand, when I decided I couldn’t do it, I just felt it was the right thing to do. I haven’t looked back.”

As people grapple with whether to pull up stakes and retire in another part of the country, there’s small margin for error. Get it wrong, and it’s hard and costly to undo.

According to a report this year from Better Homes and Gardens Real Estate, 57 percent of baby boomers say they plan to move to a new home in retirement. When asked which type of community they were likely to choose, 39 percent said a small town, like Chapel Hill, or a rural community. The next choice was a 55-and-older community (27 percent), followed by a metropolitan city (26 percent); 8 percent picked “lifestyle” communities (such as ones for active retirees, planned around golf courses).

Almost one-third of those canvassed plan to spend retirement in a different state from the one in which they currently live.

Deciding where to move entails some careful planning, perhaps compromising with a partner, and setting priorities. “No place is perfect,” Mrs. Weiner said.

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A recent report by Bankrate.com looked at several factors in determining which states offer the best quality of life for retirees, including local weather, cost of living, crime rate, health care quality, tax burden and well-being (a measurement from the Gallup-Healthways Well-Being Index that quantifies how satisfied residents are with their surroundings).

The five best states for retirement were South Dakota, Colorado, Utah, North Dakota and Wyoming. Popular retiree spots like Florida and Arizona don’t even make the top 10. The five worst states for retirement, according to the report, were New York, West Virginia, Alaska, Arkansas and Hawaii.

One big reward of relocating to a smaller home, or one where the real estate market is more affordable, is taking advantage of the equity built up in the home that’s left behind and paying cash for the new place.

If the timing is right, there’s cash left over to reduce or eliminate credit card and other consumer debts.

Moving from a high-tax state to a low-tax state is also strategic. Many people pick a retirement destination because there’s no income tax. “While income tax considerations in choosing a place to retire are important, accounting for other forms of state and local taxes that are imposed in the new locale is a necessary step prior to the move,” said Jamie C. Yesnowitz, state and local tax principal at Grant Thornton in Washington.

Florida, for example, imposes no income tax but has sales and property taxes that may be significant. State and local sales taxes vary greatly, with some at 7 percent or more. Five states — Alaska, Delaware, Montana, New Hampshire and Oregon — have no state-level sales tax.

Property taxes are generally the biggest tax burden for homeowning retirees. According to the Tax Foundation, states with relatively low per capita real estate tax collections include Alabama, Arkansas, Louisiana, New Mexico and Oklahoma, while those with high per capita real estate tax collections include Connecticut, New Hampshire, New Jersey, New York and Wyoming.

Most states give breaks to residents over a certain age, and there may be property tax credits or homestead exemptions that limit the value of assessed property subject to tax. But it’s usually in the hands of a local assessor to determine the total taxable value.

Review the total tax picture of each of your possible destinations as part of a balanced assessment of the optimal place to live, Mr. Yesnowitz advised.

For many retirees, working is also part of a retirement plan, so moving to a town with plenty of retiree jobs is something to keep in mind. A new Merrill Lynch study, Work in Retirement: Myths and Motivations,found that 47 percent of today’s retirees say they either have worked or plan to work during their retirement. But 72 percent of pre-retirees age 50 and up say they want to keep working after they retire, and in the near future it will become increasingly unusual for retirees not to work.

Work, paid or unpaid, provides a sense of purpose, being relevant, feeling connected and needed. And it helps keep the mind sharper. Researchers from the RAND Center for the Study of Aging and the University of Michigan published a study showing that cognitive performance levels decline faster in countries that have younger retirement ages.

College towns in particular are attractive places to live and work in retirement. They tend to have entertainment and sports locales and offer a range of part-time and seasonal jobs because these communities tend to be recession-resistant.

AARP’s Best Employers for Workers Over 50 winners include several universities and health care providers like Cornell University in Ithaca, N.Y.; Blue Cross and Blue Shield of North Carolina in Durham, hometown of Duke University; West Virginia University in Morgantown; the University of Pittsburgh; and Virginia Commonwealth University in Richmond.

The retired lawyers Joan Fencik Parsons, 57, and Dave Parsons, 68, aren’t looking for work, at least for now. But when they decided in 2012 to move from their home in the Lincoln Park section of Chicago to The Cliffs communities in South Carolina on Lake Keowee, the fact that Clemson University was about 20 minutes away was one of the appealing factors.

“It’s nice to have a college town close — you get some sports and some theater,” said Mrs. Parsons.

It has been a lifestyle change for the couple, though. In Lincoln Park, they could walk to the Steppenwolf Theater and to dozens of restaurants. They could walk to Whole Foods. There was an Apple Store down the street. “Here, I have to drive 12 miles if I run out of toilet paper,” Mrs. Parsons said.

The Parsons tested the waters before they packed their moving truck. They bought the property in 2008 and used it as a vacation house for a few years. “The year before we actually moved down here, we took a two-week vacation here because I wanted to see what it would be like to live in the area,” she said.

One niggling drawback. “I miss the ability to fly nonstop anywhere in the world,” she said. The tiny Greenville-Spartanburg International Airport is about a 45-minute drive away, but unlike O’Hare International Airport in Chicago, most destinations require a connection.

In addition to access to a good airport, before buying a retirement home, soon-to-be retirees and retirees should consider what their daily transportation needs will be when they are in their 70s and 80s.

That’s one reason the Weiners are now considering Portland, Ore., in addition to Charlotte and Asheville, N.C. “Don hates traffic, and there is a great light rail system” in Portland, Mrs. Weiner said. “Plus, our daughter, Laura, is living there now.”

What about the warm weather she said was a priority when they first started looking for a retirement home? “I figure we could always leave for a couple months in the winter and rent a furnished apartment in Maui,” she said with a smile.