I confess to not knowing anything about EngInSite but it's a development environment, not your installation of Perl. It It doesn't come with it's own Perl interpreter so from the sound of what you're saying it's running ActiveStates ppm behind the scenes with the force option to ignore a dependency check.

You can try opening a shell window (DOS-like environment by going to Start-> My Programs -> Accessories -> Command Prompt) and try the following two commands:

ppm repo add http://theoryx5.uwinnipeg.ca/ppms/
ppm install Crypt-SSLeay
[download]

See if that fixes you up. You may want to try re-installing the Finance::* modules after that to see if that's resolved the problem.