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1. The Sandbox has a font file (in %Fonts%). But if on the OS the font file with the same name is newer version, the Sandbox should use the one from the OS.
There is not such a build-in option for failover based on font version. It could be possible to create script that would check such a condition and do some actions.
2. If the Sandbox path is set to the same folder but can't write the modifications (maybe is a CD/DVD, maybe there isn't enough free space available or perhaps doesn't have enough rights to write there...) then it should write in %AppData%\Thinstall.
If there is a problem with Sandbox, Thinapped application wouldn't start. There is not build-in option to failover sandbox location. And it cannot be neither scripted.
3. When installing msi it should automatically erase the folder with the same project name from %AppData%\Thinstall (if it's gonna use that folder). This way you can avoid problems (like it happened to me).
I think it's issue of MSI package/template. I'm not sure if you can implement native support to delete any directory using MSI. But I think you can create some script and put it into MSI package and you can script deletion of needed directory.