Updated: The most reliable way to use Ajax is to consider each Ajax request as being atomic: it works or it doesn't.
And you (the JS running on the page) don't really get any feedback as your request is executing. So you'll need multiple calls. But be careful! Lots of overhead per call and most browsers will only execute one or maybe two at a time.
I suggest using a busy indicator to the human. You could also show a count down clock that updates at least twice per second to make it seem like something is happening.
Added:
You may also want to re-architect your solution. Eg view the update process as a batch job that the Ajax kicks off by submitting the request. Then make further Ajax calls to learn (and then) display the progress of the batch job to the human.
Comet and other "keep the pipe open strategies" can be used but are tough to get working reliably and tend to use a lot of resources. A more pedestrian polling technique can be a lot easier to get going. Then optimize if needed.