This question was asked yesterday by a customer. I am capturing the Q&A here for the benefit of all users out there.
Thanks for the question
1) At this time the Background Image function is not supported in the Drawing Sheet Creation workflow and it needs to be added into the product capabilities. I have logged this with the development team for future enhancement
2) The Background Satellite Imagery is good but not the highest resolution out there of course (that is commercially available but at a much higher cost). I captured imagery for a smaller project just fine at 96, 120 and 300 DPI, and in review of the captured images there is really zero difference between the 120 and 300 DPI imagery because the Background Imagery being offered is not of high enough resolution to gain from 300 DPI capture.
3) The Image size is the issue here. In your project the Plotbox that you defined to cover the area of the project is too large to capture a single image at 300 DPI. The PNG/PGW, TIF/TFW and JPG/JGW formats allow only a certain number of Pixels (or total file size) per image. When you define an Area of XX inches by YY inches and multiply XX x YY x 300 the number of Pixels is exceeding the limit of the image data format. In this calculation you also have to take into account Scale etc. For example, according to Wikipedia the limits of a TIFF file are 4.296GB file size total. Elseweher I read that an image is limited to 50 million pixels which at 300 DPI represents an area 408 inches square which at 1inch = 50' scale equals ~6km x 6km.
I am not 100% sure if we allow imagery up to the maximum size or whether we have some internal limit that is different to that (I will check that) but this is likely the restriction that you are hitting. Without having the project limits etc and project data it is hard for me to categorically say that this is the issue but I believe that this is the most likely.
Hope that this helps