OK, I am also a mildly inexperienced Perlmonk but here are my thoughts: all to be taken with a pinch of salt:
1. File storage: have you though about using a database such as the great MySQL instead of writing to files. This will allow you do neat things like search your diary more easily (I think).
2. Interfaces: if you know any Perl/Tk (I don't, yet ;-) then you could use that to whip yourself up a spiffy interface. The way I would do it at the moment, before I will have learned Tk, is by reading the program as a CGI script to use your browser as an interface. (This has the added advantage of making you use CGI.pm or CGI:Lite, which is my second-favourite module after DBI.pm)
As always, constructive criticism welcome.
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