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Pros and Cons for FiveThirtyEight: Their datasets are listed in order of most recently updated with those in the status of currently being updated first. The most prominent place to click will take you to the article(s) that reference the dataset. The best way to explore what the dataset offers is to click the info link and navigate to the GitHub repository that houses all its available datasets (Repository found here).
Kaggle is my go to for finding a useable dataset as quickly as possible. Data.gov is a very close second. If you're looking for a little bit of a detour that can lead you down a tangent but end up somewhere fun in the end: Data Is Plural is where it's at. BuzzFeedNews is great if you want to learn some new techniques or see the 'how' behind some number crunching. Any of these resources should get you to a useable data set, it just depends on how you want to get there...
AwesomeData is a topic-centric list of links to open datasets. This is a great place to explore a topic through the lens of data.