A quick update, switched JRiver to Asus VivoMini UN62 PC instead of my Surface which is currently on Windows 8.1 but have the same behavior if trying to output DSD to the DAC. Sometimes it would play but would come out quite choppy regardless if being a DSF file or FLAC file. Neither the processor or memory were being pushed. I tried turning off Upconvert on the Teac but that didn't change anything. If I tried a different Output mode, then usually JRiver crashed followed by the PC a few moments later. When I open up JRiver is would give me a popup about not having been properly shut down and to reset ask me to reset some of the settings.
If I change the Output to None then everything seems to play fine for my few tests but I assume everything is being output as PCM? So far I haven't had the time to really figure out the best settings and how to use it as I only get an hour ever day or two to work on it, try to play a few songs, reboot the PC a few times but will try to figure it out this weekend