#1 Rupp could break the AR and finish 10th in this one. This field is top notch and he hasn't really shown the potential to be a 58-guy. He's had plenty of chances to pop off a fast half by now and 2:06 is good but it's not 2:03, 04, 05. His 10k is one of his best marks so no doubt there's room for improvement. His 59:47 was on an aided course last year in a race set up for him. I would expect to see him go out with the 59:30 group and probably wind up top-6.
#2 Rupp might not even get the AR. Lenny Korir has run just a little slower but on an eligible course. He also took Rupp down at XC Champs to start off the year. Don't think he has gotten a mention on this thread but Rupp will likely need to beat Korir to get the AR.
#3 Two races, two week apart, half marathon and under, should be no problem for someone who has the resources of NOP. It should be noted that the half is just 3 weeks before Chicago but that is, I believe, the same time table they had last year with RNR Philly BUT RNR Philly was stated to be just a workout kind of day with bad weather. I think there must be a plan to go after a fast time in Chicago.