Is it possible, to create a encrypted Disk Image on OSX (DiskUtil or something like that) which will auto-resize by itself while writing files into the image?
I am asking because the Create Image Dialog doesn't show any option but only for fix-size-images.
Long Answer short: you should use sparse images.
Sparse disk images only consume as much space as the files they contain consume on disk. So you can create a "sparse disk image" and give it the maximum imaginable size, e.g. the size of your hard drive where you want to create the image on. If you only save 500 MB at this file, the disk image will take a little bit more than 500 MB on the disk. And if you put 5 GB on the disk image, the image file will consume a little bit more then 5 GB.
Set it here...
The only Disadvantage of a shrink image is, that it never will shrink automatically if you would delete files in it.