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http://www.motorsportmanager.com/en-us/content/making-most-steam-workshop
After you have the images in there, make sure the settings match the existing ones (when you select one, there's a list of settings in the toolbar on the right - match the examples I think).
To create the portraits assetbundle, there's a small box in the bottom right of Unity where you select the pack the files are added to. 'Portraits' may not be there, but you can type it in to start it. Then make sure all images you want put in the assetbundle have that attribute applied, and then right-click in the list of images and click "Bundle Assets" or w/e it says at the bottom (I'm going from memory). This will create all assetbundles that are in the file (portraits, as well as the others in that list).
Now, navigate to the folder for your unity file, which defaults to a folder in 'My Documents' and find the portraits.asset that you just created, and copy that file to your Motorsport Manager/MM_Data/Modding/Images folder. Then go in-game to the Steam Workshop tab, click 'My Workshop' (bottom button on the left) and make sure 'portraits' shows up there. Hit refresh if it doesn't. And then test it by starting a new career, and make sure 'Test My Mods' is 'on' (upper right of the first New Career screen).
This page on creating liveries goes into a little more depth with menus to help you understand some of it a bit more.
http://www.motorsportmanager.com/en-us/content/tips-creating-best-liveries-steam-workshop
I'm sorry. No. I didn't figure it out. I thought I was about to, but turned out I was wrong every time. It seemed unnecessarily complicated... Back in the day all one needed to do to use custom portraits in games was to crop a BMP or TGA etc. and place it in the relevant game folder, and that was it. Now, it's rocket science to figure it out :(