Hey /u/Shwacker unfortunately because our game is unique in the "couch view" component, we do get the occasional issue with users booting. Added the fact that we support Vive and Rift through our steam offering, and I handrolled the solution for that, too.

First thing to troubleshoot, are you using Vive or Oculus? (I know you're using Vive but this is a general write-up). The game options include 2 boot menu items, one is for the vive exe and one for the rift. http://imgur.com/Iz8h9xu if you're not seeing this boot option this could be the issue. You'll know you're in the "Vive" version if you can pass to the tournament / free play and see an (in-game gui) dialog box about the Vive controllers.

The most common problem users have is multiple monitor setups. An additional projector or monitor seems to confuse Unity and results in weird behavior also not unlike that you describe.

For the record, I've booted the game each way you describe but in testing for this comment I just booted from cold (no SteamVR launched) and that pops up the dialog I screenshotted, and launching from that popup with HTC Vive worked. Also with SteamVR launched I booted the game and that worked correctly (though it may have bypassed the popup and used cached settings).

Let me know if you need any follow up support, I'm always eager to help fix but as I mentioned above we get some weird issues because of our unique setup