I'm not having any problem raising Stewardship, just with normal play and only controlling i have enough food for everyone (and maybe some variety, but not to that extent). For Roguery, I'm not really sure, as I'm not walking that path, but selling prisoner as slaves also increases your Roguery skill, so it's steadily increasing, despite I have 0 focus points invested on it.
The only skills I find problems to raise are Leadership and Crossbow... so I think the rest is ok.