In order for Djokovic to pass Roger's 302 weeks he'd have to be #1 for next 3 years. He's about to turn 28. Not gonna happen unless all the younger guys decide to stop playing and let him have it. And I don't think that's going to happen. Obviously you can lose your edge and your game in a heartbeat. Look at Nadal. He started 2014 in a Slam final and won the French Open for his 14th Slam. Now he looks like he can't even remember how to play, went into a clay court semis saying he didn't think he could beat Nole and said earlier in the year that #1 is no longer a goal for him. And then look at Roger. He turned 29 and everybody started calling him old, has been, never gonna be #1 again, etc.
It's nice to have big goals and if players don't dream big then they'll never get anywhere, but as a regular schmoe I'm a realist - Nole's probably not even going to pass Connors. Eventually some young gun is going to knock him off the #1 spot just like it's happened every other #1 player. Everybody gets old. It's a fact of life. And playing the way he does - 3-6 hour matches? Unless he finds a B and C game plan and cuts his match time in half - he'll be Nadal in a year's time and lucky to last until he's 30.
BTW - please don't crap on me. I like Nole. I just don't think he's going to pass Roger. He's too old. How many guys have maintained the #1 spot from 28-31? Nobody that I can think of and I've been following tennis a long time.