Here are my 2cents:
1.Have two textfiles (or whatever) in your server as well as on app
2. app.txt stores current version, last updated, update interval
3. serv.txt stores latest version and status (alpha, beta etc) and type (next version or just bugfix)
At startup, have program compare last updated, add to interval and then compare to current date to see if it should look for update or not.
Then if it is to check for upd, it should invoke update.exe (or whatever you call) which will update necessary components (files et al)
You will be just changing server version and put something higher. Anyway you could use database with full details of what to be updated and the link to the updated file on server. This is better but you can implement whatever you see fullfilling your needs
I'm in hurry, so forgive me for any typo or broken english ;)