1. Do you like the community where your vacation property is located? Is development being planned in the community in the future which would detract from your enjoyment of the property?
2. Can you see yourself coming here on a regular basis over the next several years?
3. Is your property an easy drive from your present home or is it a major production to get back and forth?
4. Many people plan to make their vacation property their full-time residence when they retire. Would this vacation property fill that need for you?
5. If you don’t plan to retire there, is it important that your property also be a good investment and appreciate in value in the short term?
6. Are your children enthusiastic about your vacation property? If they want to bring their friends along, will there be enough room?
7. If your property is in a development which has a community association, familiarize yourself with the association’s governance and how the association fees are calculated.
8. If you do not plan to rent out your property, you may want to hire a local management company that will keep an eye on your property if you are not going to visit it for several weeks or months. This is especially important in places where your property needs to be “winterized” before the weather gets cold.
9. If you rent and manage your property yourself, it’s still smart to hire a reputable local property manager. They are your eyes and ears when you are not there, and can act as your agent when a renter has an issue and you are not there to deal with it.
10. Familiarize yourself with tax regulations affecting your vacation property, in particular with respect to any applicable tax deductions you can take.