I've (temporarily) admitted defeat for the watercooling portion of this build. After getting the wrong thread screws for replacing the radiator and finding out that my 90 degree compression fittings don't allow the radiator to sit at the top of the case due to interference from the GPU, I've switch to air cooling since I had a Noctua L12s on hand for the second Winter One case I'm getting for the living room. This install was much easier, although cable management leaves a lot to be desired with the inflexible ribbon cables, and I think ultimately custom cables are going to be a necessity for this case, but I was expecting that.
Ultimately for an "I need this PC working now" build, I'm happy with it, and the side panels hide my terrible cable management very well.
Also for anyone else with a Silverstone PSU, just an FYI that it's an extremely forced fit if you want to have the PSU fan facing outwards. Probably worth getting a new power extension on order.