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Business and Investment Expense Documentation Even though there may be no question as to the deductibility of a business or investment expense, it may be disallowed by the IRS for lack of supporting documentation.   Tax Aspects of Owning a Second Home Many taxpayers currently own or plan to purchase a second home. You may view your second home for personal pleasure only or as an investment for tax benefits and appreciation. Perhaps you are somewhere in between.   One-person 401(k) Plans for the Small Business Owner One-person 401(k) plans are becoming increasingly popular for businesses that employ only the owner. Given the right circumstances, such plans can allow a large amount to be contributed on behalf of the owner while maintaining flexibility in making contributions in future years.