Vacation or Second Homes

Sometimes, actually a lot of times, people think they don’t have the ability or resources to accomplish a certain goal, and then it truly becomes unattainable. A timely quote for this might be, “People don't plan to fail; they fail to plan.” (This was most recently said by a REALTOR in New Jersey, but don’t think he was the first.)

First, you have to ask yourself what you really want—possibly this will lead to workshops on goal-setting, or minor, then major, soul searching, then therapy. We’ll leave that up to you, but we do recognize that for most people making transitions can take time. Fast forward and move onto your second home strategy.

A down market of new and existing home sales spells opportunity, and the IRS allows for certain benefits, if you plan well. Do you plan to make it your future retirement home? Then area will be especially critical. Have you factored in your upkeep and expenses for maintaining a second home vs. an annual summer rental? Are you living in the desert and wishing for ocean breezes—if you’re calling on a coastal listing and it’s 108 degrees where you live now, you might be calling out of desperation (see “Fools Rush In” at the link) rather than a good long-term plan.

Have you talked with your tax accountant or attorney first to be aware of how you can gain or lose with the IRS—how many days you may or may not rent out the second home, how to avoid the Alternative Minimum Tax or minimize it, or how your Subchapter S corporation through your business can benefit you. Have you thought about your 1031 exchange and capital gains factors if you decide to turn this into an investment property, or vice-versa? If you have an vacation investment property you may be able to exchange it or convert it later to personal use:

“A section 1031 exchange lets you sell one investment property and defer the capital gains if you put the proceeds into another. You'll have to rent out that new property, too, to qualify for the tax deferral. But after renting the property out for a year, you can convert it back to personal use. There's still no tax until you sell.” (Jeffrey Schnepper is a New Jersey lawyer and CPA, personal finance columnist and the author of several books on tax strategies.)

You could be considering a family home, a smaller cabin, a condo or townhome or a duplex or a triplex near the beach where you could be gaining income on the other units. The initial planning stages may put you through some work, but it’s better than buying a property and later losing money on it because you bought it in that dream like state while you were on vacation already.