I started with weaver, then added botanist to get weaver mats. It's good to keep blacksmith, leatherworker and weaver ahead of other classes so you can keep making gear and tools for them. For HQ you need the Leather and carpentry level 15 skills. Buying gear and mats from the market board will break your bank pretty quick. The higher you get the more cross class mats you will need, and the more expensive they are. At the moment I am trying to level everything fairly equally. Except fishing culinary or armorer. Generally as soon as I need something I don't want to buy, I start leveling the class that has it.