Unsurprisingly, the "Who's Hiring" almost perfectly tracks the "Software Development Job Postings on Indeed in the United States" data from the fed, though it doesn't go as far back.
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.
Same! You may enjoy "Everyday Engineering: Understanding the Marvels of Daily Life" from The Great Courses [0]. It's free on Kanopy through many libraries.
After this, do a bit of research on goal programming or other approaches to multiobjective optimization. It could really help and depending on the approach, it's not that hard. It usually just adds a bunch of constraints or some precompuations to an already existing set of in/equalities for your model.
ALLOCATING CONFERENCE DELEGATES TO WORKSHOPS: A SPECIAL TIMETABLING PROBLEM --
"The problem of assigning delegates to workshops at a conference can be formulated as a timetabling problem. Such an assignment must take into account the preferences of the delegates, as well as the number of participants each workshop can accommodate. This paper will report on a heuristic solution technique for a special case of such a problem."
[1] https://hnjobs.mathieularose.com