The Plan So Far (in rough)

[DarkCloud_PK]

As for the my thoughts on the plan, it seems like deja vu from 2004.
Remake the server from something that is 'unusable' and build from the ground up.

Only now it's 2009. There is no strong dev team to do any sort of project like this. There are barely as scripters as compared to 2004. The drive to script is lower, the management has since went inactive.

Sounds like you're trying to do the same thing 5 years later with a lot less than what you had 5 years previously, and with more inactivity.

However, it could be simple to keep the current overworld and fill it up with content, while phasing out the bad custom systems one by one in a progressive nature.(Though I'd like to keep the nickname system the most).

There's a less possible route to failure, why are you going for the definite failure?