Al Capone tried avoiding taxes too, and it didn’t work out too well for him. We can deduct any expense, but in the event of an audit you will have a much HIGHER chance of success if you show reasonableness from the start. It is not our advice to deliberately deduct expenses that are unreasonable with the hope of negotiating somewhere in the middle- on the contrary, the IRS auditor or Tax Court is likely to view your expenses as extravagant forcing you into a bad situation. We are flexible, and we try to maximize your deductions, but we also want to maintain honesty, fairness and reasonableness- this is to your advantage.
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