Convenience to Your Home - San Diego Airport makes downtown perfect for this!
First, determine if the location is convenient enough to make a vacation home appealing. How close is the vacation destination to your home? While it is great to "get away," the reality is that you may not wish to fly every time the opportunity to go on vacation arises. Especially with the rising cost of airline tickets, you may wish to choose a location within a short drive of your home.
Of course, sometimes driving is not an option. If you long for the convenience of a tropical retreat, but you live in the mountains of North Dakota, then go ahead and purchase somewhere tropical. However, before you do, check your local airport to ensure that regular flights are available.
Ongoing Appeal - Supply in Downtown San Diego is low with Demand High!
Your vacation home is an investment that you will use year after year. Before you buy, make sure the area has staying power for your family. You need to buy in an area where your family will want to go annually for vacation. No matter how appealing an area may be the first two or three times you visit, you are investing in years of vacation. Is there really enough for your family to do to be interested long term?
The answer to this question is going to depend largely on your family's vacation style. If you are a lounge-on-the-beach-and-do-nothing type of vacationer, then a cabin on the beach in a remote area is ideal. If you like to see sights and do activities, then you will want to ensure that the city or town nearby has plenty to keep you interested — or even that the vacation home is located near a major amusement park or big city.
Potential Rental Income - Studios rent for $1500+, 1 bedrooms $2000+, 2 Bedrooms $2400 up!
Another consideration is what you will do with your vacation home when you are not using it. Do you want to rent out your property to earn some income when you are not using it? While the majority of vacation homeowners do not choose to rent out their property, if you think you may want this option, you will need to buy in a popular destination where vacationing is common. Consider shopping near the mountains, ocean, a lake or a river.  Zillow predicts hike in San Diego Rental Prices for 2016.
Potential Investment Value - Prices for Downtown San Diego predicted to rise by 10% in 2016!
Vacation homes are, at their most basic level, an investment. Evaluate the location to determine if it will be a wise investment with growing value.
In 2014, the number of vacation home sales rose by 57 percent, which is a peak since 2006, according to CNBC. The vacation-home market accounted for a full 21 percent of the homes sold that year as well. This means there is currently a strong market for vacation properties.
Yet that does not mean a strong market will remain for your vacation property. For that information, you will need to research the area where you are buying with the help of a skilled real estate agent. Choose an area where sales prices are on the way up and where a continuing demand for real estate is projected in the coming years.
Family Interest - Unless you want snow, downtown San Diego offers everything imaginable!
Finally, find out what your family thinks. Do they picture themselves vacationing with you, annually, in the same spot? Does the city have enough to appeal to them as well as you? Remember when buying a vacation home you are purchasing your family's memories for years to come. Make sure those memories are tied to a location everyone loves.
With a vacation home, you can build the memories that your family will cherish for a lifetime, and you will also be able to invest in your future financial security. Choose your location wisely, and you will find a vacation home is a welcome addition to your family.  marsha@sellsandiego.com 

Original article by:  Tim Anderson and Harry Chandler who founded The Chandler Anderson Group, REALTORS®