A couple of years ago I developed a small "handy-dandy" C# Winform .NET/SQL Server pilot application for a client that we really thought would be used for a while and discarded. It runs on a laptop that travels all day in a truck and returns back to the office at night, where the data collected is sent back to the server via XML over a LAN connection.
I realize that there are more elegant ways to synch the data, but that's not an issue here.
As the business has evolved the application has become more popular and now there are a bunch of laptops in use with more soon to come.
In addition, the client sees more opportunities with the application, so enhancements are becoming more frequent.
In the original design I included a standalone update application that looks on the server for data structure or program changes, brings them over as needed and updates the data structures and the business application.
Someone has to be told to run the update application and run it.
That same update application sets up the business application on the laptop when it's first put into service.
That's too cumbersome and it's not going to work anymore.

We need to see that changes are required from the laptop business application itself (no problem there), terminate the business application without losing the fact that an update is needed (how?), run the update (how?), and restart the business application using the new .exe's (how?).

I have some ideas and I've seen some things on the web, but nothing is lighting my fire.
What's the best way to do all that smoothly with .NET? (VS 2010 SQL Server 2008 R2)