Server: Use the undocumented (but handy) readcmd instead of localcmd to parse skill files instantly. This will avoid the bug of delayed config loading. That's the theory.

src/server/entry.c

@@ -252,10 +252,7 @@ void worldspawn(void)
 	lightstyle(9, "aaaaaaaazzzzzzzz");
 	lightstyle(10, "mmamammmmammamamaaamammma");
 	lightstyle(11, "abcdefghijklmnopqrrqponmlkjihgfedcba");
-
-	/* sometimes we have extra overrides that the original does not
-	   provide. so we execute our mod-specific config here */
-	localcmd(sprintf("exec skill_%s.cfg\n", cvar_string("game")));
+	Skill_Init();
 }
 
 float ConsoleCmd(string cmd)

src/server/skill.c

@@ -14,6 +14,16 @@
  * OUT OF OR IN CONNECTION WITH THE USE OR PERFORMANCE OF THIS SOFTWARE.
  */
 
+string(string cmd) readcmd = #0;
+
+void
+Skill_Init(void)
+{
+	/* sometimes we have extra overrides that the original does not
+	   provide. so we execute our mod-specific config here */
+	readcmd(sprintf("exec skill_%s.cfg\n", cvar_string("game")));
+}
+
 float Skill_GetValue(string variable)
 {
 	float skill = cvar("skill");

src/server/skill.h

@@ -15,4 +15,5 @@
  * OUT OF OR IN CONNECTION WITH THE USE OR PERFORMANCE OF THIS SOFTWARE.
  */
 
+void Skill_Init(void);
 float Skill_GetValue(string);