My dear Nephew Wormwood,

Let not this recent victory go to your young head, nephew.  Tax complexity is but one tool.  We must remain vigilant at all times on many fronts or our Taxpayers will slip away from us. 

Continue to suggest to your Taxpayer that there is no need for documentation.  Lull them into thinking that they will not get audited.  But don't let them know the truth that all the while we have succeeded in having the IRS increase the number of correspondence examinations. 

We are foiled, Wormwood, if the Taxpayer starts using simple programs like Xero and Mint to track their personal expenses. 

Absolutely do not let your taxpayer find out about Expensify and it's integration with Bill.com to help them keep up with expense documentation. Your Taxpayer is basically lazy in these tax matters, robbing them of their precious tax dollars. 

Wormwood, you should suggest that their poor records, particularly for auto mileage and meals & entertainment, is not a problem.

Charitable contributions are a ripe area, Wormwood.  More IRS regulations, and details, lots of rules on both your Taxpayer and their CPA.   (The hiring of a CPA should be avoided at all costs Wormwood).  There are many opportunities for them to lose their precious deductions, Wormwood.  And I am happy to inform you of a recent IRS victory costing millions where your Taxpayer failed obtain a simple sentence on the receipt - "No goods or services were received in return for this contribution".  Fertile indeed, Wormwood, for us to rob them.

 Don't forget, Wormwood, your Taxpayer does not handle change well.  Use it to your advantage.

Your adoring uncle,

Screwtape

P.S.  Holden Moss can help you with tax and business documentation automation, or register for email tax alerts here.

With due acknowledgement to C. S. Lewis for The Screwtape Letters.