Ryan needs to retire in 2018/2020 if he wants to run for President in 2024. No incumbent Speaker will win the nomination and definitely not the general.
Yup. The longer he's in the job, the more it'll damage him, as it becomes clear that he can't really wrangle recalcitrant members any better than Boehner could.
The sooner the GOP realizes that its base is crazy, the sooner this will happen. Look at how much money they had to spend in 2014 just to ensure that a repeat of 2010 wouldn't happen. Sad but pathetic that the GOP has to fight its own voters in order to remain a viable party. A part of me does feel about an ounce of sympathy for Paul Ryan because he does seem like the kind of guy who genuinely does want to make government work; his problem is that he belongs to the party that DOESN'T want the government to work.