It starts to look less like a gift, and more like a fee for service business arrangement. Thats especially true if you structure the “gift” in such a way (i.e., up to gift tax limit every year for x years) to avoid tax consequences.

So such a gift could make Bob run afoul of some state and/laws for being an unlicensed broker or financial advisor. It may also trigger IRS violations.

Admittedly, since we’re dealing with a hypothetical, we have a third-person omniscient view into the motivations of both parties, and there are legitimate questions about their actual motivations, what their actions suggest about their motivations, their knowledge of the relevant laws and regulations (some violations may require the parties to “knowingly“ engage in a violation), and what a trier of fact could ultimately prove. But based on this fact pattern, a nice dinner and a fond farewell might actually be the best gift.