My pleasure Sir...I know all too well what it's like to look for something and have it there under your nose. Happens to me all the time since I like to tweak around with this game a bit (I do that with every game on my PC, lol!)
Though since installing GWX I do less of that, but still enough to get me into trouble, lol.
As to your other question, since you've basically set your starting renown in both files to zilch, I would assume it would make it more challenging, but since we all what happens when you assume, I'll let the old hands here chime in on that.