After some experimentation today with the latest Strawberry Portable Beta 2, it would appear that it now passes all required functions, and all previously noted bugs are now solved.
I was able to install it to a drive, start the CPAN client, install Padre from scratch with all dependencies, and all of the .bat files in the /perl/bin directory correctly launch the related Perl scripts.
With nothing left remaining to do, we should see the final stable release in the next couple of days in a special mid-cycle Strawberry release.
All hail portable perl on windows!