A Hardy Pioneer needs to be working inside the settlement for the option to appear once the student 'graduates'. As for Veteran Soldiers, I'm afraid you can't train them in educational facilities. Sucks. It was one of my main strategies in the original game.
Under the current system, training cheap (European purchase price) professions is highly discouraged. You're much better off training things that cost a lot (1500+) than the simple types.
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