I'm not sure I'm getting you right.
Do you want something like:
Category 1
- link 1
- link 2
- link 3
IMAGE
Category 2
- link 1
- link 2
- link 3
IMAGE
...
If so, for each image you want to place
you can create a category and when you setup it specify that
it should display an image.
The add one link in that category with your image.
If you want something like:
Category 1
- link 1
IMAGE
- link 2
IMAGE
- link 3
IMAGE
you can setup that category as an image category
and only add an image for every other link.
I hope you get what I mean
I'm not aware of any plugin to eazy this up, maybe someone else does tho.