Routing, Multiple Rules and Duplicate Fields Bug?

Hi-
I'm running into a problem that may just be a bug in my understanding. Here's what I'm trying to do: I'm setting up a form that will send subscribe request emails to a mailing list manager based on a drop down field. In this case, I'd like people to be able to subscribe to a mailing list based on the classroom their kid is in. Should be a walk in the park, just use routing to send a message based on the value of the drop down.

The place I am running into trouble is with a duplicated field. If a parent has multiple kids in the school, each in a different classroom, they should be able to subscribe to all of the lists they need from the same form. Same deal, I thought. Duplicate the drop down field, set routing rules so that a separate message goes out for the choice in each of the duplicated fields and I'm golden. I figured this would work because in this thread:

Question re Email Routing

Carl mentioned that a new message gets fired off for every rule that matches. [quick aside: that's a useful piece of info that I don't see anywhere in the official docs on routing]. This is exactly what I'd like to happen since I need a separate message to go to each of the subscription signup addresses.

I'm unfortunately not seeing that behavior in 1.6.1. so I'm wondering if I'm seeing a bug in either my understanding or GF (probably the former). Even though I have two rules that should match, I'm only seeing one email being dispatched (which correctly shows the two values for the duplicate field in {all_fields}). I've been doing a bunch of testing, and I still can't quite work out just how GF is choosing which rule actually fires. I'm just pretty sure that only one is being generated.

This is fairly easy for me to work around in the meantime by just using two fields instead of a single duplicated field but that feels a little less elegant than using the cool new duplicate fields functionality in 1.6+.

Thanks for any help you can offer.
-- dNb

P.S. Bonus related question: Does GF currently write a log file anywhere with notification debug info? I'd love a text file some place that had lines in it like "[timestamp]Sent email to user@example.com with subject "blah"". Right now I'm using my own server logs to try and suss out what GF may be sending, it would be much cooler if I could get that info from GF directly.

I think my question is related to this. I, too, looked in the documentation on Notifications but don't see anything that indicates if every routing rule that matches gets sent an email or if only the first rule that matches sends the email. I have not tested this yet because I have a list of over 50 routes that I need to finish entering. But in my example I want only the first rule that matches to route the email.

My example has a form with a format pull down and a department pull down. I want to put my format rules first since they should take priority over the department rules. It might be useful as an enhancement to allow the administrator to indicate whether the first or all route rules that match should send an email.