Hey @jpowell – thanks for the feedback. I really appreciate your attitude on this. We know there are a couple spots here that are incredibly frustrating and we’re thinking about whether there’s even more we can do to make this better after our upcoming 1.1 release.
For 1.1, I’m happy to let you know we have some fixes coming that should make this much better. We’ve added some more powerful editing features to the track grouping screen, so you’ll be able to enter track and disc numbers, group the whole set, and nail the ID. This should eliminate the need for the widely-hated up and down buttons, which will still be available for basic matching, but won’t be needed for giant sets requiring millions of clicks.
For now, my advice would be to get your files as close as possible to the original release, and organized as per @jeremiah’s post here.
Also, I’m always on the lookout for painful examples I can torture myself and the team with 
@jpowell – would you mind dropping a link to the Angela Hewitt album’s page on AllMusic?
Thanks!