Segment Running
 

I have a question about my plan to do a segment run for points.

I'm looking to book BOS-LGA roundtrip three times to take advantage of the bonuses for the route, and stacked with the points from the fare, and the lucky 7 bonus, makes the runs cost effectively 1 cent per point for me.

Now, I noticed that I can save a bit on taxes if I book BOS-LGA-BOS-LGA-BOS on one ticket. Will I have any problems with this crediting the bonuses? I didn't see anything in the True Blue or promo T&Cs that would suggest it wouldn't post, but I thought I'd post here to be sure. Will each segment count toward badges? I think I might actually earn the "New York - Practically a Local" badge which would make this run even less than 1cpp.

Will the system hiccup on me if I book this as a multi-city and try to check in?