I was actually looking at converting these over to VARBINARY(MAX) since I've seen some deprecation warnings about IMAGE/TEXT/NTEXT/ect. column types. My question on that is when they insert the image...

Yes, and we actually had someone from MS come out to configure the FILESTREAM options on the server and they were not successfully able to get it configured and working...

I think it depends on what you are doing. Are you wanting to regenrate the master key? Are you just wanting to regenate the DB Certificate? If you are just...

Just so everyone knows, restarting a second time allowed the DB to be shrank. Not sure why it didn't happen with the first reboot.