Ok I did it now this way
+ Complete fresh Install of Civ4 (Steam Legacy enabled)
+ Fresh Install of c2c 38.5
+ Installed PPIO v0.5.9.5.3 for C2C v38.5
+ Started quick Game to get the User Settings filled up
+ Quit Game
+ Edited the C2CTheme_Common.thm File to get my Font:
GFont .Size0_Normal = GFont("Expressway","Regular", 13, GFlags(GFontFeature, GFC_FONT_ALPHA), 0, GRectMargin(2));
GFont .Size0_Bold = GFont("Expressway","Semi Bold",13, GFlags(GFontFeature, GFC_FONT_ALPHA, GFC_FONT_BOLD), 0, GRectMargin(2));
GFont .Size1_Normal = GFont("Expressway","Regular", 15, GFlags(GFontFeature, GFC_FONT_ALPHA), 0, GRectMargin(2));
GFont .Size1_Bold = GFont("Expressway","Semi Bold",15, GFlags(GFontFeature, GFC_FONT_ALPHA, GFC_FONT_BOLD), 0, GRectMargin(2));
GFont .Size2_Normal = GFont("Expressway","Regular", 17, GFlags(GFontFeature, GFC_FONT_ALPHA), 0, GRectMargin(2));
GFont .Size2_Bold = GFont("Expressway","Semi Bold",17, GFlags(GFontFeature, GFC_FONT_ALPHA, GFC_FONT_BOLD), 0, GRectMargin(2));
GFont .Size3_Normal = GFont("Expressway","Regular", 19, GFlags(GFontFeature, GFC_FONT_ALPHA), 0, GRectMargin(2));
GFont .Size3_Bold = GFont("Expressway","Semi Bold",19, GFlags(GFontFeature, GFC_FONT_ALPHA, GFC_FONT_BOLD), 0, GRectMargin(2));
GFont .Size4_Normal = GFont("Expressway","Regular", 24, GFlags(GFontFeature, GFC_FONT_ALPHA), 100, GRectMargin(2));
GFont .Size4_Bold = GFont("Expressway","Semi Bold",24, GFlags(GFontFeature, GFC_FONT_ALPHA, GFC_FONT_BOLD),200, GRectMargin(2));
+ Saved File
+ Started up Game to look if the now Font is working
aaaaannnnnd
nothing
(Even chose Wingding Font after that too see if i am just blind and didnt notice it, but nope)
I think i am just missing a Step