On the off chance anyone seeing this is interested, I have a solution uploaded 
as part of a module I wrote for screenplay and stageplay writing: 
https://github.com/cjayross/drama.mkiv/blob/4a9b2576c8630fd03352d95f99456092f6e21190/drama.mkiv#L480

The solution ended up being very detailed and tightly coupled to this 
particular problem. However, the general approach was to use box registers to 
capture the portions of dialog marked using a command sequence (`\continue` in 
this case) that designates acceptable locations to insert a page break in the 
dialog. The markup is then placed into the document in pieces with each 
placement testing the `\pagetotal` against the `\pagegoal` to measure whether 
the current piece will fit on the current page.

This solution had to up using `\synchronizeoutput` as opposed to 
`\triggerpagebuilder`. I'm not sure why there's a difference in behavior 
between the two, but the former seems to fix bugs where the `\pagetotal`s would 
output the measure of the previous page rather than the current one -- leading 
to sporadic page breaks.
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