Hmm, fair enough. Jagr was, indeed, iconic. But I feel his icon status began to grow as he aged and the overall sentiment increased. Early on, Jagr was booed mercilessly in many arenas, was considered a diver and crybaby... and in cities like New York and Philly, fans would whistle at him every time he touched the puck. Until Mario hung them up, Jags was generally in his shadow, even owning the "Mario Jr." moniker. He was also criticized heavily in many circles for his mostly disappointing stint in Washington and ended up bolting to the K after a short stint in New York. Jagr may have been iconic in a way during his NHL career, but he was polarizing and often criticized.
Ovechkin, on the other hand, was practically an icon overnight. Even before he arrived in the NHL, he was getting tons of attention, and he appeared on the scene with Crosby post-lockout. He was an instant sensation, and even his mirrored visor was as iconic as his flamboyant and contagious goal celebrations.
For me, the difference between Jagr and Ovechkin is that Ovie was universally beloved right off the rip. Even the hard-nosed and vicious Philly fans had a soft spot for Ovie... perhaps the only Cap they've ever liked!! Ovie is so likeable it's scary. Even though the NHL tried to position him as the Darth Vader to Sid's Luke Skywalker, the fans never took the bait... because Ovechkin was way too likeable to be cast as a heel.
I think the appreciation for Jagr has grown over the years... mad respect paid to him for his genuine love of the game and commitment to playing into his 50s. He deserves ALL OF IT!! But I'm going to venture to say in about 5-6 years if/when Ovie is still playing in the KHL, his legend will have grown even more... when he's in the HHOF as the greatest scorer in hockey history.
He received the most RW All Star Game votes in the East his second year in the league when he was, barely, a PPG player and not even a first line player on his own team.
So yeah, Ovechkin was great from the get-go, Jagr was not, and that's the point -- Jagr was a star before he was a hockey star.
And while his hockey status with the Pens grew, he kept being the most popular RW in the league (or the East) for a decade, rockstar-popular in Pittsburgh.
Yeah, he had some tough times for about four years in a career than spanned almost three decades and he had Don Cherry talking crap about him.
But that's the point.
In my opinion, through hardships, hero to zero, media and fans turned against him, then winning them back, then calling it quits for his own reasons -- having fans and pundits drool over his comeback and his legend growing -- then pissing the Pens fans off again and playing for whoever he wanted to play -- he became iconic. And mysterious, because he will forever have his "what if" factor. And the number up the rafters with the Pens -- a team he made love him, hate him, kinda love him, kinda hate him, then finally retro-love him again.
All those things you mentioned actually make him more iconic, his myth stronger, and his career more colorful. Just like Ovi's "he's my friend" moment and his 'gram pic with you-know-who actually make his personality more interesting.
In terms of personality/impact/status/mystique/story though, Ovechkin is silver to Jagr's gold.