Using Upfront as a Theme for a Membership/Course

I am looking at changing a site them over to UpFront since we are having some issues with Gravity Forms with our current custom theme. I just wanted to find out a couple things before I jump into making the change.

Here is a screenshot of our current site - as you can see it is a members area where we have people go through the course and submit assignments. We use BadgeOS to let them submit the assignments and grade them etc... We also use Wishlist Member for the membership management. We have about 250 students and they pay a significant sum to join so I don't want to screw anything up. Luckily it is hosted on WPEngine so I created a staging area and I can play with Upfront to see if I can make it work.

Before I do though I was wondering if you think a similar layout is possible with Upfront, because all of the starter themes, none have a sidebar. The other thing I was wondering if the lesson completion checkmark is possible with Upfront.

Final things are does anyone have any experience with using Upfront with Wishlist and are there any problems? Same with BadgeOS.

Thanks so much!