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Going from memory here, but browsers have traditionally handled <br>'s in lists slightly differently. I believe I had it strip off one line due to that behavior. Changing it is somewhat of a big deal as it will break the historical formatting. As it does still allow you to add trailing breaks, I might leave it.

The issue of what happens when you edit is more related to the first bug, though I suppose that both bugs are related: HTML to BB code line break conversion. I'm going to mark this as a duplicate mostly because the issue from both of those bugs requires a full rewrite of the line break handling code, which would hopefully resolve this case as well.