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so OP you dont need to assign any role for your main character
If you don't assign anyone to a role then you will be doing it all personally (your character can fill all roles at once). That means you get the skill gains/exp, and that any perks you've taken will be in force for that role. I usually keep all the roles through the entire game, with the exception of the period when i assign my siblings to quartermaster to raise their steward skill.
Aye. Engineering is so ridiculously easy to train with just personal ballista use in sieges that there's no point in ever hiring a companion as engineer, especially since they don't come with even average engineering skills to start with. Medicine is more difficult to train, though, and the benefits are substantial. A good surgeon is probably the only role a typical player should always try to find a companion for.
Medicine is easier than it used to be, but yes, it is one of the harder skills to train to high levels. One of the easier tricks you can use is to go out with a party that's nothing but your companions and deliberately get them all wounded, then go sit in town while they heal. As long as you have companion death turned off they provide you with an inexhaustible supply of wounded to train on with no risk.
Once you get to that point, sure. It's the first 75 points that take a long time, especially if you don't spend a focus point or three on it. The biggest bottleneck is that you need wounded/healing checks to keep it moving up, and you don't get enough of those until you're fighting big battles constantly. You also aren't getting gains during peacetime, which is the time I'm most likely to throw all my troops into a garrison, take away my companions gear, and make them charge into looters.
If nobody else is assigned to a role, the role is assigned by default to the party leader. So to answer the original question, "That is correct. All Scout, Quartermaster, Surgeon, and Engineer skills that have an effect tied to that role will only function when the person who has that skill is in the role". With nobody else assigned to those roles, that is the party leader, which is relevant because OP asked about "any of the quartermaster skills i have unlocked.