Dana definitely wants Khabib to win. He has the chance to be a very dominant long-reigning champion. His broken English combined with serious matter-of-fact Russian attitude makes him very marketable in a way. Having a dominant Russian champion could help the UFC lure more top talent from Russia and Eastern Europe, where there are a lot of such fighters, especially at 205, that seem to have minimal desire to sign with the UFC. Khabib gaining recognition as champion could change that and help the UFC shore up their flagship weight classes and reverse the trend of watering down their product with so many manlets and WMMA fighters.
Conor has no real desire to fight Khabib or Tony. It is just too big a risk of severely damaging the allure he has crafted as his brand. He has about a 10-15% chance of knocking either Khabib or Tony out in the first few exchanges of the fight. If he's not able to do that, the inevitable happens. Tony latches onto him with one of his crazy standing chokes and drags Conor to the ground, where he will easily be embarrassed and forced to tap, likely even quicker than his record-setting millisecond tap to Diaz's rear naked choke. Khabib takes Conor to the ground with little resistance like he does to all his opponents. From there, he absolutely controls fish-out-of-water Conor and brutalizes him. Conor hopes that the referee stops the fight fairly quickly, so he can spin some cockamamie excuse about it being stopped early, like he did after the Mayweather fight, or invent some other ridiculous bullshit like how he was inefficient with his energy against a fighter that had no training camp.
Conor will keep being Conor, teasing like he wants to fight when in reality he is just trying to keep his name in the news. He will only fight again if the reward greatly outweighs the risk, or very safe fights, where he has an advantage and there is very little risk that he will get embarrassed. For example, more fights against journeyman Nate Diaz. Angling to fight Frankie Edgar on short notice after a new opponent was already announced. Proposing a 165-lb division to fight GSP for a belt. Bullshit like that.