My opinion only so FWIW applies:
Fallout 4 looks and works much better than Skyrim, so since the remaster is basically Fallout 4 with a new skin over it, I think at least as far as VorpX/VR is concerned, it too will be a better experience overall.
Thats not to say that Sky looks anything less than spectacular once you get it tweaked now, because it is awesome defined. But with Fallout 4, you are already starting off several steps ahead of where you start with Skyrim (legacy/current) to begin with. DX11, full VRAM/memory access, better models and base textures, better draw distances/cell changes, better shaders/rendered (and it shows) etc.
There are sure to be some problems concerning modding… SkyUI being the big one. Hopefully someone carries on their work. The one good thing is that the remaster and legacy versions will be separate installs so we can always keep playing and tweaking the older version as well.