noglider Strava said it was only a 6 mph wind, but it sure felt like more to me. Looking back, I think it was a combination of not being well-rested in the morning and the headwind. When I went out for a "lunchtime mission" I felt stronger, and when I rode home (uphill) I felt stronger too. That was after drinking coffee and sitting in my desk chair all day.
Re. your bike setup, how is the lock prevented from bouncing out of the basket? I'm thinking you could run the shackle around your seatpost or seat tube with the lock bar securing it to the basket. I like the lugged frame and springy steel fork. I bet it's a nice ride. I look at modern steel bikes and I'm sure they saved some weight and gained some vibration damping by going to a carbon fork, but the ride is almost certainly better with steel, shaped like yours.
Is that a dynamo hub I see out front?
BobbyG I agree. Having a descent ruined by headwind is worse than uphill. For one thing, the hill blocks a climbing headwind somewhat. For another thing we weren't going fast to begin with, so it feels like nothing much is lost.