Shape Collage Pro is the tool i've used for collages - althought the shape part of it never really excited me. Set a grid (or not) and dump the pics in, its fast; and yes still a bit of editing required but it is quick. I think only the paid version allows editing in Photoshop but well worth it if you have a few to do
WidsMob Montage is a software that can arrange any number of photos within any container, all you have to do is to load the music Band logos and determie the container (in your case it will be simple rectangle) and set the spacing between the logos and if they interlace or simple tile.
and in your case you shoud select a small number of photos in row and ...
This should work with any raster software which supports layers and layer masks, such as Photoshop, GIMP or Krita, etc
Take (or find) a suitable photo, and create a layer mask to remove its centre.
Duplicate the layer, and select the bottom layer. Scale it smaller.
Duplicate and merge the layers and move this to the bottom of the layer stack
Select the ...