I don't know if he struggles selling the school as much as he made some strategic errors in recruiting following the Baby Boilers. For whatever reason, he started going after a different style of player - more long, athletic, and raw - and went away from the skill guys. And it had terrible results. He also missed out on a couple big 1A targets during that stretch and had some highly ranked guys (all three of the Johnsons and the 2013 class all come to mind) never really play up to that level in college.
His recommitment to prioritizing skill, and shooting in particular, has coincided with this recent resurgence. He talks about getting a great shooter in each class and that allowed him to build one of the best shooting teams in the country the past two years. Now, having back-to-back All Americans will make most rosters look pretty good, but he's gotten much better about stacking solid, if not remarkable, classes on top of one another.
I don't ever expect Purdue to overtake IU as the trendy/cool spot in the state, but I think as long as Painter can continue getting solid "Purdue guys"* and sprinkling in a big get every couple years, I think he's going to get over that hump.
*this cliche never gets old