Tipping as Rental Income Deduction

"To be deductible, a business expense must be both ordinary and necessary. An ordinary expense is one that is common and accepted in your trade or business. A necessary expense is one that is helpful and appropriate for your trade or business. An expense does not have to be indispensable to be considered necessary."

Link: http://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/Deducting-Business-Expenses

I'm a CPA - while flarf's quote is correct, i wouldn't do it, how much are you tipping him? what kind of documentation? i assume it's cash because he is employed by the building and can't work for you. If it's a lot it will be a read flag, if it's a little, why bother?

Um, why wouldn't you do it? Keep contemporaneous records. You can deduct tips at business lunches and in taxis and at hotels and wherever; tips are a legitimate business expense. What exactly is the downside?

Call it a bonus and you can deduct it for sure

You can also deduct if you have a home office, but only something like 7$ a person.