Gonna go with option 2 for now:
heavier winter tights with some windblock, which should cover me for the extreme end of things and as cold as I'd want to ride in (before wussing out and riding Zwift
).
Next if I find myself doing lots of cold weather riding, I'll add some more "nice to haves" kit - ie Rapha Core Winter tights, and/or Rapha Classic Thermal Bibs + warmers or similar. Both look great and honestly being here in NYC will probably get much more use than a dedicated deep winter piece, that's really only needed for a month or two.
Thx for the help.