Hi Jerry,
What version of the Oculus Rift Runtime are you running? I seem to only be able to run OR Runtime v 0.4.4 with Outerra. There is an internal version of OT working with 0.7.0, but it hasn't been released yet. Try installing 0.4.4.
Always make sure your NVIDIA and OpenGL drivers are up to date.
The TDR error you are experiencing could be related to a number of other issues. A good place to start is deleting end.cfg and world.cfg from your data directory (typically located at: C:\Users\YourName\Outerra\). Once you delete these files and run OT again, they will be re-generated. Sometimes when you update to a new version of OT, these config files get corrupted or are in some other way out of date. If that doesn't help, one you generate them again, open up eng.cfg in a text editor, and try setting img_cache_num_slices = 5 at the bottom (don't go any higher than 5, default is 2).
If none of that works, you can try deleting the default.cam file from the campos folder in your data directory. Not sure why this effects the NVIDIA timeout, but I've recently had luck with deleting this file in trouble shooting the same error for someone. You might want to backup a copy of default.cam before you delete it permanently.
Best of luck!
Regards,
Uriah