help, with problem #1? Using the packages prepared for your particular flavor of *nix is often the answer.
And self-help, using a search engine such as big G, MS's entry, DuckDuckGo, etc., often helps you find that answer (Google with search terms "Ubuntu Crypt:SSLeay Perl" provided the source linked above.
To deal with "'cpan' command no longer works for me when I am the root user" you may wish to consult the various sources of Ubuntu-specific information... and when you do so you may wish to explain "no longer"" (implying that it once did "work" but stopped at some point). IOW, what did you change just before you started having the problem?