This should be corrected

banned

If you saw issues on the site this am, Rackspace had some network flapping going on, dropping packets. Should be fixed now.

I'd start here with the Stairways, they are designed to help you get started. Once you have basics, pick up Itzik's book and learn more.

You can capture the output of the script and execute it directly instead of using xp_cmdshell.

You would need to do the inserts one at a time.
WITH myTally(n)
AS
(SELECT n = ROW_NUMBER() OVER (ORDER BY (SELECT null))
FROM (VALUES (1), (2),...

No hurry

Good summary from Lowell, but I'll add a couple simple thoughts.

Column encryption is is designed when you trust the server, not the client. You need to trust admins...

apt-get update
apt-get install mssql-server

I like Linux updates.

we could use another one, so please feel free.