The Lost Regiment Re-Boot Character Generation (OOC)
No game system is perfect, especially when trying to keep things simple and focus on role playing.
Classical Education is a skill that will be quite advanced and may not exist on the world of Valdennia, like many other skills the Yankees will bring with them (Engineering, Natural Science, Medicine). If this is a skill you are interested in then you should begin the game with it, as there will be limited options to learn this skill from scratch once the game has begun.
Other skills like Melee and many Hobby or Vocation skills would be very easy to learn throughout the game.
The skill system works by characters earning X Points and then spend the X Points (and time, with a teacher) to acquire or improve skills.