Just today I've started using Drupal for a site I'm designing/developing. For my own site http://jwm-art.net I wrote a user-unfriendly CMS in PHP. My brief experience with Drupal is making me want to convert from the CMS I wrote. A CMS whose sole method (other than comments) of automatically publishing content is by logging in via SSH and using NANO to create a plain text file in a format like so*:

    head<<END_HEAD
title   = Audio
keywords= open,source,audio,sequencing,sampling,synthesis
descr   = Music, noise, and audio, created by James W. Morris.
parent  = home
    END_HEAD

    main<<END_MAIN
text<<END_TEXT
Digital music, noise, and audio made exclusively with
@=xlink=http://www.linux-sound.org@:Linux Audio Software@_=@.
  END_TEXT

image=gfb@--@;Accompanying image for penonpaper-c@right
ilink=audio_2008
br=
ilink=audio_2007
br=
ilink=audio_2006
    END_MAIN

info=text<<END_TEXT
I've been making PC based music since the early nineties - 
fortunately most of it only exists as tape recordings.
  END_TEXT

( http://jwm-art.net/dark.php?p=audio - There's just over 400 pages on there. )

*The jounal-entry form which takes some of the work out of it, has mysteriously broken. And it still required SSH access to copy the file to the main dat dir and to check I had actually remembered the format correctly and the code hadn't mis-formatted anything (which it always does).

I don't want to drop all the old content (just some), but how much work would be involved in converting it, factoring into account I've been using Drupal for a day, have not written any PHP for a couple of years, and have zero knowledge of SQL?

How might a team of developers tackle this? How do-able is it for one guy in his spare time?