I know this part of the game never will please everyone no matter which way the devs go; between wanting no failure and wishing for unexpected results, there can't be compromise. Mods, cheats and save reloads are the answer, unless these can be adjusted with a very detailed difficulty setting.
In my case it's not wanting zero failure, it's more a case of either my PC has the skills or she doesn't. When she kinda sorta has the skills but they're only 20-25% of the equation (at least at this point) and a dice-roll does the rest then I don't see the point of investing in skills. But as I said I don't come from a D&D background and I'm likely to be missing the point.
