Hey Tom, this got me thinking about a few things.
I found the Admin option called "Use first heading for pagenames", which seems to totally solve this.
In the pages where I had an actual heading tag all of the display of those page titles were nice names with capitals and punctuation. Problem solved - except it only worked for a few minutes and now I am getting an error called "Security Token did not match. Possible CSRF attack." and it reset this option back to default (off), so I have to sit down and figure out what's going on with that. It worked great when it was working though :(
I don't think we're going to find a lot that is going to be perfect for transferring the discussions. But there is a nice discussion plugin that I set up and tried on one of my other installations that can be automatically added to the end of each page - I was figuring that I would copy and paste any relevant discussions to a box above this discussion area and then people could continue on with whatever they needed to talk about. Not the best solution but, well...