NEW YORK (Money Magazine) - So can you, too, afford a beachfront condo or, say, a Victorian in the San Francisco Bay Area, if that's more your style?

Tally mortgage and tax expenses, then add upkeep, such as condo maintenance fees, landscaping, golf club fees. Also compare the cost of living in the area with that where you live today. If you're looking at a second home, add in the cost of setting up and maintaining a new household, from furniture and appliances to a second set of utilities and taxes.

You may even need to purchase a separate wardrobe to keep there.

When house hunting, don't worry about finding your dream home right away. You can always trade up later, says Nathan Booth, senior adviser for the Senior Real Estate Specialist Council, an international group that certifies real estate agents with special skills for working with older buyers.

If you have benefitted from the real estate boom in your first home, you can easily put your equity to work in a second. Or you can trade down to a smaller home.

If you're buying a second home now -- especially one that you will use only occasionally until you retire -- consider buying a property that you can rent out when you're not there.

EscapeHomes.com CEO Hehman says more second-home buyers are looking for rental income.

"Buyers want to see a property's rental history," he said.

Success at renting requires pulling together a lot of details, which may make it worthwhile to hire a property manager. Check the going rates in your area; they can range from 10 percent to 50 percent of rental income.

"Match your destination to your lifestyle, then sharpen the pencil and make sure your choice makes economic sense for the long run," Hehman says.

Here's a quick list of questions you should ask yourself before settling on any destination:

Community: What type of neighbors do you want? Are you craving cocktail-party chatter about the latest hot restaurant? Or would you rather discuss what everyone's grandchildren are up to? Do you want to attend classes or lectures at a local college? If you're in a resort area, does the town roll up its sidewalks when the season is over?

Ease of travel: Would you like to be near a hub airport with several airlines to choose from and lots of nonstop flights? Or within an easy drive of family and old friends?

Access to work: If you want or need to keep working, is the local economy thriving? Do the businesses where you plan to live value older workers? Do you prefer driving or taking public transportation to work? Is telecommuting a possibility?

Medical care: Are there teaching hospitals and a healthy representation of specialists close by? Does your health plan offer a choice of in-network doctors and health facilities in the area? If not, your selections may be limited, or you may need to consider alternative insurance.

Safety: This is especially important if you plan to travel for long periods or if you're a nightlife afficionado.