There is no "grey" area here. I am quite sure that what your former accountant was referring to was the meals and entertainment deduction. It is not just a general business expense that is allowed.
The IRS does not require a receipt when your business meal or entertainment expense is less than $75 per expense.
You still must maintain a record of the following five facts related to the deductible event:
1) WHO did you eat with or entertain? i.e. the names of the people and the nature of their business relationship to you
2) WHEN did the entertainment occur? i.e. the date
3) WHERE did the entertainment occur? i.e. the name of the restaurant or other venue
4) WHY did you meet? i.e. a description of the business purpose of the meal or event
5) HOW MUCH did you spend? i.e. the dollar amount
You should record these five facts in a log. Having met the IRS substantiation requirements, you can then throw away the receipt if you wish. In the event of an audit, you'll be covered.
The expense applies to meals and entertainment expenses incurred when you are with someone with whom you have an existing or prospective business relationship, regardless of whether you are in town or in overnight travel status.
While receipts are not required for these expenditures of $75 or less, they still should be legitimate expenses that you incurred. So for that reason I would have to say that your former accountant was being a little over zealous with these deductions -- particularly if he was deducting this same expense for every day of the work week. If you would happen to be audited by the IRS, I think they would find it very questionable that you had an entertainment expense of $75 every day and not one single receipt for any of them.
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