I know @LeeGriffing has a lot of opinions on this.
My general rule is to keep anything after the “N” 7 syllables or less, but I also like them to end in “RB” so that can be a challenge!
Scott currently has a Mooney with the tail number of N72JC and I thought that would be a perfect tail number for Jack Cochrane if he had a 172, but Lee doesn’t like it.
This is a current discussion on a group text between @Dr.Badass, @LeeGriffing and I that I want to move over to here so that we can get some more input.