Many people do it. They have a main residence in one area of the country and then they have a second home someplace else like Florida or Virginia and go there to spend warm summers and lay on the beach. Great on the surface. Many people do it. It is trendy.
Here are two questions to consider.
1. Is Your Second Home at Work Making Money for You?
This means a consideration for its value on the open market. It should be increasing in value. You should be able to sell it today for a profit. Most people see their homes through sentimental eyes and that is understandable. But. Remember a home is an asset in much the same way that money is. Money is not for buying things as most people think it is. Money's purpose is to make you more money. If your money is not at work making you more money, then it is not doing its job. It is the very same thing with a house. A house is not just for living in comfortably. A house's purpose is to create even more house for you. In this case the worth would be called equity. Has the house been improved upon since you bought it? Has it been kept up-to-date with the latest electrical codes and green standards? Are the floors in good shape and the paint fresh? Whenever you walk into your second home you should always feel like you would buy it all over again and you want anyone else who sees it to feel that way, too.
2. Are You Using Your Second Home Often Enough to Justify the Expense?
Most people do not want to consider this because they look at their second home as a luxury and feel that it will naturally not be used like their first home. Not a good idea. Homes are for living in. When they are not being used the wrong things tend to accumulate such as water in the radiators, frost in the pipes during those long winters when you are comfortable in your primary home, overgrowth on the landscape and bugs in the wood. Each time you open the house for yourself you must undo all the damage accumulated while it sat empty. Over time this adds up and, in addition, it is not fun to tend to. Consider renting the property or having a live-in caretaker to maintain the property while you are away, to keep it toned until your return.