There will probably be a new checkpoint in each release.
My understanding is that removing centralized checkpoints requires confidence that the network is decentralized enough. In Peercoin this is a slow process that depends on new coin generation and the number of people minting. In NuBits the shares have been distributed in such a way that minting is already decentralized enough (no one was able to buy a very large amount of shares, the undistributed shares do not mint, there’s a strong incentive to mint, etc.).
Also, Jordan doesn’t want anything centralized in the code (see Implementing In-App Alerts for important announcements).