This is an interesting thread and most of my >35 year experience is in this 
area, or related ones.
IMHO as they say, you don't stop development to re-do a UI.  Here's what 
you do:
1) Adapt the files to a new port, a re-write.  Gets easier every day. 
 Parallel development.
2) You identify a specific key feature that has some problem and that can 
be improved.  You make a nice easy link into a new GUI element (a modern 
style menu perhaps like a cell phone's)  or a guided dialog.
This can be integrated into the existing system.  Hit a button and get a 
better GUI interface.
That's my 2 cents.

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