Ok, flags and shields.
In both cases you start with a 2 dimensional "flag" graphic. 324x216 works best. There are several photoshop "template" files you will need (I will get all that stuff together in a zip file and post it ASAP). When you have the "flag" and the template files you will need to run a Photoshop "action" by loading? a .atn file. This file is basically a script that processes the 2d "flag" and outputs a finished HOI2 Flag or Shield.
I do not have photoshop so I reverse engineered a Python script that does an analagous procedure for Paint Shop Pro 9 using the .psd templates. I believe that there are Photoshop readmes with the template. Also, a user named Mad King George on this board has a website with all the templates and instructions.
Leader Pics
find your headshot of a leader crop it to a .720 ratio (final size needs to be 36x50 pixels), resize the pic to 36x50, then paste it as a new layer into the leader_template.psd file that I will post. Then drop the picture layer below the border layer that is in the template. (the existing layer is the white frame that goes around the pic). Then save it as a 24bit bmp file named appropriately for whatever leader you want it to be.
Counters
Here I use a tool made by Andreas Schmitt (KeldorKatarn). Basically you can open up an existing counter, increase the color depth to 16million colors/24bit. Then edit as you please. You can reduce a "flag" to 14x9, or a roundel to 10x10 and paste into the counter. Save the counter as a 24bit bmp. Then go to My Computer and drag both your counter and the counter prototype (in zip file) onto the exe file (in zip) it will produce a new counter called counter_new.bmp that is in the correct game palette. Delete the 24 bit one you made and rename the new one and then put it in the correct game folder. Keldor has a good readme in th zip file
Event Pics
Easy, just open an existing one. Wherever you see green (green=255, red=0, blue=0) in the image, will be transparent in the game. Just find an existing one that has the right aspect ratio for the image you want, paste your image over it, then save as a 24 bit bmp with the name you want.
Now for the files
Leader Template
Flag Template
Shield Template
Counters