Don't forget that the "real" way getting away with it is to have your relatives buy thousands of options on the stock that you're an insider with. Nobody will ever figure that one out, right? This actually happened "back in the day" and many "relatives" are probably still paying the money back and recovering from prison sentences.
When I was an officer and on the Board of US Elecitricar, back in the 1990's, our stock was trading around $2-$3...and we were headquartered in the small town of Sebastopol, CA, right next to the Santa Rosa municipal airport. We were developing Electric cars and motors, and had an alliance with GM. Well, we had set up a meeting with the "big guys" of General Motors, including the then CEO, Roger Smith. Well, there were dozens, if not hundreds of the "locals" who had purchased stock in our Company over the years. It took about 45 minutes to unload the GM jet and drive to our building, in which time, the stock traded as high as $12 or more as I recall. The rumor mill was sure that GM was going to buy our Company, LOL. Well, GM didn't, never had a plan to, they just wanted to see the AC drive electric motors in a working prototype since the motors were developed by one of their subsidiaries.
I had zillions of shares, did not sell any of course (tempting, LOL)... I think if I had, that would have been bad thing, and that my "karma" would have divorced me altogether.
If it feels wrong, it probably is But we all dance to different drummer.
FWIW,
Don