Place multiple files from Mini Bridge in Photoshop document
When you work with document that need additional files to be placed, Photoshop allows you to insert only one file at time through Place command in File menu. To insert (place) multiple files at once you can use Bridge or Mini Bridge. Here is my suggestion how to insert multiple files from Mini Bridge and to have best possible preview of that document at same time. I assume that document is open in Photoshop and Mini Bridge icon is visible at palettes on the right side of screen. First ensure that top most layer is selected, because otherwise you may not be able to see placed files. Press F key twice to enter Full Screen mode.
Navigate mouse to the right side of screen to appear panels where Mini Bridge icon is located.
Press Mini Bridge icon to expand and activate this plug-in.
Navigate to files on your computer, and select all files you want to insert in document (hold down Ctrl while clicking).
Click and drag selected files into document (you will se plus sign below cursor while dragging), then release mouse.
All selected files will be placed into document (one above another) with bounding box around of top-most file, now press Enter couple of times to accept and proceed to arrange and reposition them.
With Move tool active (V), press Enter once and Options Bar will appear on top of screen. Check Auto-Select option and Layer from drop-down list. To get rid of Options bar, press Tab twice.
Click on top-most placed file and drag it to new location. Do the same for other placed files (web icons in this case).
To be continued with Precise position and resize multiple objects.
Further reading and videos (free):
Introducing Mini Bridge by Matt Kloskowski
Bridge Help / Mini Bridge
A product used in this tutorial: Adobe Photoshop CS5 Extended