Oh give me a break with reasoning like that. You hire a handy man to do some work for you. You pay them cash for that work and you claim that makes that money a gift because you didn’t have a written contract. What reality do you live in.
First of all, I never said anything about a WRITTEN contract. If the handyman charges you $250 for a project, you have a binding agreement (in most states, I am sure) for $250. If you pay him $275, how exactly is the extra $25 documented on a financial statement?
And how does this change if you give him $250 plus a case of beer?