You'll need to use a scripting tool such as AutoIT or IExpress to package the installer, options and responce recording file.IExpress is part of windows and can create self-extracting EXE - https://technet.microsoft.com/en-us/library/dd346760.aspx
From http://stackoverflow.com/questions/4354617/how-to-make-get-a-multi-size-ico-file there are some standard size for ICO graphics and you can merge multiple sizes into one ICO file with ImageMagick or ICOfx (30 day trial)256x256 will be saved as 32...
You could use a combination of the RegEx tests here: http://stackoverflow.com/questions/7905929/how-to-test-valid-uuid-guidAnd methods to execute RegEx in InstallScript here: http://ulanoff.com/blogs/codeshack/2009/07/20/regular-expressions-in-instal...