Solomon,
I have successfully deployed some SQL CLR for EXTERNAL_ACCESS to allow Web service calls from SQL Server. Since I am a DBA and not a .Net programming expert, I asked for a code review from someone on my team who is. She pointed out that they had done a .Net application deployment some years ago, and they had signed the application with a .pfx file. They had a problem with the application about a year later because the certificate in the .pfx file had expired.

For my development and deployment process, I created a simple assembly that had one class with no members, and I had Visual Studio create a new .pfx file for it. For my real assemblies that I use for SQL CLR, I import that .pfx file into the project for signing. That way, once I have created the asymmetric key and login, all other assemblies based on that .pfx file will install and run.

I checked my .pfx file with "C:\Windows\System32\certutil.exe", and it has an expiration date about 9 months from now.

Question 1: Are my SQL CLR procedures and functions going to stop working 9 months from now?
Question 2: Will I be able to sign future assemblies after 9 months using that .pfx file?
Question 3: Is there a more permanent solution?