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larose

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https://mathieularose.com

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Regarding the HN to sqlite part, I'm writing a "syncer" that continuously updates data from HN to a local sqlite database. Its goal is to enable anyone to have a local copy of the HN dataset to build various projects (like yours) on top of it. I'm about to release it as an open-source project and would love to collaborate to make sure it supports your use case. I couldn't find an email address in your profile, so please reach out if you're interested.

Your problem is a scheduling problem. It has been well studied in operations research [1] / mathematical optimization [2].

Basically, you formulate your problem as a integer programming model [3] and use a solver [4] to solve it. You should check PuLP [5].

You can also ask your question at OR Exchange [6].

[1] https://en.wikipedia.org/wiki/Operations_research

[2] https://en.wikipedia.org/wiki/Mathematical_optimization

[3] https://en.wikipedia.org/wiki/Integer_programming

[4] https://en.wikipedia.org/wiki/List_of_optimization_software

[5] https://pythonhosted.org/PuLP/

[6] https://www.or-exchange.org/