Your situation is what it is and obviously you should have considered how this would look prior to taking this course of action. Too late now so you just have to see how it plays out.
Most people seeking entry on the VWP are asked a couple of routine questions then let in. Obvious we tend to see the extreme cases more often here as most people travel with out a second thought.
I am never one to suggest somebody does not use a Lawyer, having said that somebody here on a Student Visa, assuming they are not trying to get a GED, suggests that they can DIY.
Well the onus is on them and the worst possible case would be a waiver and not sure I have seen that. They would have to show Misrepresentation.
Lawyer and mention of 90 days suggests they do not know what they are doing.
The only problem I can think of is if you forgot to mention you were married when applying for a Student Visa, having said that I do not know exactly what the process is for Canadians.
I suppose the first thing to do is find out what happened to SERVIS.
Will it look odd absolutely.
Will you be quizzed about it, I would think but no way to know for sure.
Are you going back for language or your Masters?
Then when they arrive and they have the I 551 stamp in their passport, nobody can forecast the future all you can do is put yourself in the best situation.