Real Estate Deal Analysis & Advice12yFollowPre-planning for tax purpose: rental or 2nd-home characterization?Rich ThomasInvestor · Gig Harbor, WA · Member since 2013 · 9 posts · 2 votes I put almost 2-years of searching for a property in Arizona - lots of expenses involved. Made two purchase offers during that time. The third offer closed and I now own the property - we've stayed there last winter and I was planning to rent it - but have not. Instead, I now wish to sell it. How should I characterize the sale? As a second home or a rental? Can I capture the two years of searching as deductions against capital gains or as a cost basis? 0Reply7 views