I had a very long career in real estate, much of it was spent in the resort property business which I really loved. Buying a second home is a great concept to sell but may or may not be a great concept to buy into. Here's an alternative plan to owning a second home, instead of having one home, in one location that requires maintenance (i.e. spending your cherished time away from work doing things like mowing grass and cleaning out gutters), or having a monthly overhead and ownership dues that never go away. This antiquated concept also ties you to one location that you are obligated to visit, even if there is something else you'd rather do. Also, the vacation home market is one of the most volatile real estate investments you can make. 

I have six second-home locations that I try to visit as often as possible, with none of the above problems or obligations. Here's a simple plan: Let's say you would love to have a really cool place in San Francisco. Step one, go online and find your two or three neighborhoods that look really cool to you in San Francisco. Then book your ticket with enough time to spend a day in each of the favorite areas that you have selected. Walk the streets, check out the restaurants, check out the access to the other cool parts of town, transportation systems, and any lifestyle tips or areas that are important to you. Within that neighborhood there will be one or two really cool places that catch your eye to stay.

Going in, look around, talk to the management, get the rates during the different seasons of the year. Try to figure out where the two or three bathrooms in the hotel are for your purposes. Remember most places have a high season, swing season and off season, and rates can vary dramatically!

Spend one night in each of the top two or places that you have picked out, and really see the place from the inside out.
After you have spent at least one night in your top places, narrow it down to your very favorite! For me my favorite place is Hotel Boheme in the South Beach area of San Francisco. It's an old Italian neighborhood in transition, and Hotel Boheme is were Allen Ginsberg and many of the best poets stayed and worked. It's classic! I consider that my second home in San Francisco.
Always book it way early in the year, and I have two of my favorite rooms picked out. I always ask for one of those two rooms, because within each hotel they're going to be rented or more desirable than others.

I want to go to San Francisco, I know exactly where I'm going to stay, I know the management and when I call ahead they remember me. I have my favorite restaurants picked out and I know how I'm going to get anywhere else in the city that I want to go. The big bonus, I have no contractors to deal with, no maintenance, no overhead, and no guilty feeling that I should be spending more time at my second home if I had a fixed location. I have favorite second homes in Manitou Springs, Colorado; Galveston, Texas; San Francisco, Seattle, New York City, and New Orleans.

Try this idea, before you decide to invest in a fixed location second home!

©Kem Anderson 2017

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