No KJ, I don't think filing as a business is overkill. Even though Russel Fox said filing as a business involves having to pay self employment tax, there are some additional taxes for retired folks that maybe be over looked. Okay, you have to run the numbers which I haven't done.
The additional tax is on high earners who have to pay more for their Part B and Part D Medicare premiums. I don't know if you ever heard of above and below the line, but these taxes are based on adjusted gross income which is above the line while itemized deductions are below the line. If I included my gambling winnings in other income it becomes part of my adjusted gross income, and my MAGI would be in the $266,000 to $334,000 range. I would have to pay an additional $220 every month for my Part B and Part D premiums. If you file as a business (Sch C) both winnings and losses are above the line and you don't have this problem.
KJ, you seem to think I'm some kind of idiot when it comes to taxes. I majored in accounting in college and took both individual and corporate income tax courses which were an easy Ace for me. I'm no tax expert, but I do know a lot about income taxes which Rob Singer thinks everyone he is clueless.
Here is a link to these taxes for folks on Medicare.
https://www.ssa.gov/benefits/medicar...-premiums.html