One thing you can do, quite easily, is have your program print comments about what it's doing (right before calling $ssh->capture2() or whatever), and of course it can print any captured output or error string afterward, so your output can look something like this:

Connecting to remotehost...
Connected.  Attempting to log in...
Logged in.
Sending command: cd /var/foo/wibble
Command succeeded.  No output.
Sending command: cd -
Command succeeded.  Output:
/home/jonadab
Sending command: cd /directory-that-does-not-exist
Command FAILED.  Error information:
cd: /directory-that-does-not-exist: No such file or directory
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If you want to get fancy, you could even use Term::ANSIColor and display different things in different colors (e.g., output in green, errors in bright magenta, comments in white, and commands in bright yellow, all on a black background; or whatever colors make you happy).