I lived in Nova Scotia for 10 tears and winter looked just like your photo - grey skies, chilly wind and for me, a miserable climate. It hovered just below freezing but that wet cold felt worse. Not sure if your area gets that cold though.
I moved to Alberta in 1981 and get 20 below, tons of snow and 6 months of winter every year. TBH it's not Hawaii , but I prefer it out in Alberta because it's a dry cold with big blue skies.