At first, the hill didn't seem so bad near the cemetery. It could have been all the houses and trees blocking the wind, since by the top, near the Masonic Manor, I struggled to keep moving forward. That tall building has a way of funneling wind directly at you no matter which direction the air is moving. Kinda weird.
But after passing 52nd St, I coasted downhill almost all the way home. It's a fun bike, for sure, but we'll see how it handles the winter weather. Or rather, how I handle the bike in winter weather.
Edit for day later experience: The wind was WAY worse on yesterday's commute home. Going up that Leavenworth hill, I seriously almost got off to walk. It was bad enough I hopped onto the sidewalk just so I wasn't at crawling speed in traffic. But yesterday was probably the one of the 5 or so worst wind conditions we'll get during the year. Other horribly windy days are usually straight from the North or South, so Westbound on Leavenworth isn't so bad. One bad part about the single speed though, even though I made it up the hill, I think I tweaked a back muscle just to make it those last 2 blocks. It's not bad, just a little annoying.
So I'm still a go for keeping it simple on the SS, but the toughest days of winter are yet ahead.