Think it all the way through.   Many second-home buyers expect to own their properties for the rest of their lives, but few vacation properties are that flexible.  The cozy lakeside retreat that´s perfect for a childless couple might be too small or hazardous for toddlers or too isolated and boring for teenagers. Similarly, your high-schooler might revel in a hopping beach front location that will be way too congested and noisy once you´re retired.  In fact, the very attributes that draw you to a place may turn out to be its biggest disadvantages. A secluded place may be too far away from a hospital or help if you have medical conditions.

Security, maintenance and insurance.   It is twice a much work to take care of a second home.  Do you want to go away only to clean, cook, and repair.  Can you afford to have the second home maintained.  That is the ideal situation, to have a cleaning lady, a lawn person, a handy man.  Since you are likely to be away from your second home for long stretches of time, you should take extra security measures. Consider enlisting the services of a local handyman or a neighbor to collect mail, keep an eye on the place and take care of routine maintenance jobs such as leaf and snow removal and mowing the grass. Ask a neighbor or the caretaker to park his or her car at the house occasionally, and use light timers to create the illusion someone is home. An alarm system is a good idea as well. Premiums for homeowner´s insurance are typically higher for second homes, because the chance of a break-in is higher. If fire hydrants and stations are remote, premiums can rise further. And if you rent your second home out, the cost of insurance can rise as much as 20 percent to reflect the increased risk.

If your second property is a condominium, most of your insurance and security needs will be covered by your condo fees. You will still need liability and contents coverage, however. 

   Contact a real estate professional.   A real estate professional is your eyes and ears in distance places. "You can do a lot of things without a real estate agent, but there is a point when that picture you saw and that virtual tour isn't enough. I'm a Realtor and when I was looking to buy in Palm Springs and I needed a Realtor I could trust who I knew would help me. A Realtor can highlight areas of interest. One of the things I've learned is that a resort real estate agent is very different from a regular real estate agent in a resort area. You have to rely upon someone who knows the area," rather than someone who merely sells homes.

Approach joint ownership with caution.  Many people who don´t feel they can afford a second home on their own decide to split the purchase with relatives or friends. And many of them regret it.  It´s not just scheduling conflicts that cause problems. People who are compatible in every other way can have screamingly different ideas about how often the lake house needs painting or who should be responsible for the pipes that burst last winter.  It's great for family bonding when together, but who is going to get mad when it's dirty, somethings broke, or the last thing used wasn't replaced.

Purchase through a area or resort specialist.  People selling in a resort area know more about a particular area and typically take it very serious that business comes from the outside. So buy from somebody in that area.  They know  the traffic, they know the pluses and minuses of the area.  Outsiders' questions are are quite different from those inside the area. It's only a half hour, say, from Miami to Ft Lauderdale, but make sure you are not working with someone who lives in Detroit who wants to sell a home in Florida.