Hey Marty,
a. The main application would force update itself using wyUpdate at runtime and restart (even before the main screen)
wyUpdate can't update your app when it's running (in fact, no updater can - it's an impossibility on Windows). But it can minimize the time the end-user sees the update progress. Specifically using the free AutomaticUpdater control.
Plus, you can modify the branding of wyUpdate to match your application's icons / artwork so the user always knows what's going on.
b. At the main main screen, the main application would call each of his installed plug-ins to update themselves.c. When (b), some of those plug-ins would also use wyUpdate to update themselves.
See below.
1) being able to force often small updates (e.g. changes in the main .exe and some .dlls) without the need for the installer screen to pop up each time. Is there a way? Ideally I would have my own "in app" update screen for the download and installation steps and restart the app when it's done.
If you're making a .NET app, you can use the free AutomaticUpdater control to do just what you described. Namely, when your app is running and it finds updates it does all the long work (download, extracting, patching files) in the background. Then the next time your user runs your app wyUpdate completes the update. Afterwards it starts the new version of your app.
2) Is the "Library/plug-ins" updating scenario supported and/or feasible? (i.e. an assembly that call its own update - using its own wyUpdate etc - and let the hosting application know when some updates are ready to be installed or have been installed)
Yes, it's possible. You only need a single copy of wyUpdate.exe, but you'll need separate client.wyc files for every plugin. You can then use Silent update checking along with the parameter -cdata="C:\location\to\client.wyc" for each plugin.
In fact if the plugins are in a sub directory you can even update the plugins with restarting your app.
3) Would it be a problem to have multiple plug-ins (think Dlls + resource files) to update at the same time or would having multiple wyUpdate.exe to run simultaneously would be okay just as long as there's no MSI installations?Would I need to update them serially?
So long as they don't try to update the same files or registry it should be fine to run wyUpdate.exe concurrently. wyUpdate has no such limitation.
Tell me if this helps.