Bridge not working

When say, "...editing with masks" you are referring to Camera Raw I assume. This issue has been discussed in the Camera Raw Forum and has been acknowledged.

See here.

I will pass commenting on Bridge crashing, there's not enough information (what your OS is, where the files are located, to name a few potential issues), but I will take a crack on the your mask issues.

First off, the masks are part of Adobe Camera Raw and are only associated with Bridge because Bridge (and Photoshop) have ACR plugins for them to access ACR. Nonetheless, I'll see if I can help you with your disappearing masks.

If you are working on raw images, no one can change a raw image with any adjustments. Rather, all adjustments are placed in what is called a sidecar file: a separate file that sits in the same folder as the original camera file. Regular ACR adjustments are held in a file with an ".xmp" suffix, while any of the mask adjustments are held in a different sidecar file with the suffix ".acr." 

The trick with sidecar files is that you MUST keep them together. If you move a raw image out of a folder without bringing the sidecar file(s) with that image, when you open that image up again, any changes will not appear. If you move that file back to where the sidecar file(s) are (or them to the files current folder), the changes will appear. 

Now, let's say your working with DNG or TIF files: in this case, ALL sidecar files (both xmp and acr) are contained in the file as if the file were a folder. So you never see them, but they are there.

Lastly: JPG files: JPG files are also containers but not as robust as DNG or TIF files. They contain the xmp files but not the acr files. So, back to keeping tabs on where the sidecar file is from the image file. You need to keep these together.

BTW, one other issue with either TIF or JPG files: let's say you did a great job of enhacing a file and want to share it with anyone. So, you thake that JPG file and email it to a friend. If that friend does not have ACR, all they will see is the file BEFORE you made any changes. This is one of the "gotchas" with ACR. If you want your friend to see the final file, you need to do a Save as… for that file and send them the newly saved version of that file.

I hope this helps!