I won this dubious award myself when I secured a great lease option deal on a gorgeous lakefront home but made the HUGE mistake of having the option start right away (just at the beginning of the off-season)  instead of once I found a tenant-buyer.  I made 5 months of payments out of my own pocket on an empty home while I tried to find a tenant-buyer.  In the end that mistake cost me over $7,000 and a lot of stress.   

Lesson learned: I should have either made my contract contingent on securing a tenant or waited until the start of the on-season to begin the contract. 

For more information on avoiding other risks in lease options see Chapter 4 of my book Investing in Real Estate with Lease Options and Subject-To Deals.

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