I recently upgraded computers and reinstalled CS6. I can no longer search my files based on keywords or file name.
If you have reinstalled your app on a new machine you also have to index the files for a proper Bridge search.
Go to the Bridge Find command (menu edit / find) and from the search criteria choose a keyword you know that exists. Be sure to point the source to the main folder your files are in and also select the options to include non indexed files and subfolders, This may take some time but that is only once, after this has been fulfilled it should work again. And your keywords are persistent (they don't appear in italic) I presume?
And YES, the keywords are italic. I did not know what that meant.
This means that they are in your file but not in your Bridge Keyword tree. Don't know if you have your old system software backed up somewhere but you are able to export and import keywords list using the small menu icon top right of the keywords panel.
If you have your old User library still somewhere the keyword file is in this path User (your user name) / library / Application Support / Adobe / Bridge CS4 and inhere should be a file called Adobe Bridge Keywords.xml
Export provides a text file and you can import that also easily.
But I don't know if Keywords have to be persistent before they can be searched in Bridge, logic would be that it should not matter and just reads the xmp data from the files itself.
Maybe a reset of the preferences might help or even a manual deleting of the Cache file can bring a solution.
Just my opinon: I find Bridge a little too daunting for my simple mind. I used to use iView, which I found very simple and easy to use. I may see if it's still around.
I'm not the one to judge your own qualification...:-)
However you are comparing two different things to my opinion and memory. iView was indeed a wonderful DAM application but had qualities Bridge does not have and vice versa. iView had its limitation as did Extensis Portfolio for me. I'm on a Mac and a few years ago I discovered that Canto Cumulus had a new Single user version. At the times of MacOS up to version 9 I used Canto to great satisfaction but they did not provide support for OSX 10 until recently.
While Bridge is not very reliable for use as a Digital Asset Management (to my opinion) Canto Cumulus is. But Canto is by far not as good at all the other tasks Bridge can do so I use Bridge up on to the moment the files are finished and ready for archive and I use Canto only for archiving purposes.
iView Media Pro has quit a history since. The developers had done a good tasks and decided to sell their baby. Unfortunately they did choose Microsoft as buyer. As often Microsoft did promise a lot and delivered nothing. The application (then renamed to Microsoft Expression Media) was killed softly. But Phase One regained the rights and called it: Phase One Media Pro.
Since I'm am a happy Canto user again I did not try this version but you can get a trial here: