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I'm trying to decide which bar course to get, and wanted your thoughts about which one to get.

I'll be studying with my roommate and both of us will be taking the bar for the same state. Does it make the most sense to get the same company's course (so that we'll be on the same track)? Or would it be better to get different courses (in case one lecture doesn't make sense)?

(Both of us have firms that are paying for the courses, so we're not trying to get by with just a single course even if that'd be an alternative.)

You're over thinking it. Get the same course and watch it together. If you get Barbri, there will be very little that "doesn't make sense". You will certainly benefit from having a close friend to go over the same material with. Getting two courses will just be too much in my opinion.

So, when I was studying for the bar, My roommates and I all took different bar classes, but one of them and our (collective good friend) took the same class together. He lived down the street and those two studied together frequently.

Generally, it doesn't matter because after about a month, you'll all be completed with the lectures and be on the same page. Sometimes, the alternative view might help with a finer point of law, but remember, on the bar, nuance isn't that useful. Getting the basics down, guessing on the fine points and creating a reasonable IRAC will do the trick.

Will it help? Assuming you both can study effectively, it likely won't hurt. But there's no major benefits one way or the other. I preferred to go at my own pace and I generally slept in, while my roommate and our friend preferred getting up earlier. Those study issues might be more important than the course.