I've been rolling my clothes for years, and I discovered an improvement. I was rolling them individually. Now I lay them all out flat on the bed, one garment on top of the other. Then I make one big roll. This resists wrinkles even better!

These questions come up all the time, and the answers here are excellent. The funny thing is, you will work out your solutions yourself.

Some of us have charts of what to wear in various kinds of weather. It's written down for some of us, and it's mental for some of us. Since you're starting in May, it's a lot easier.

In many places, I find that traffic starts dying down quickly by about 8 PM, and can be quite low by 10:30 So, good lights with attentive riding, and that may well be enough.

You do have a pretty short ride, so adding an evening mile or two might not be bad. I've been known to add a hill or two in the middle of my commute in the past, just for fun.

Lately, however, at least by the Strava challenges, I seem to get in far more flat miles than climbing meters.

...is evil and will eat your soul.

The true path of righteousness is one of these on a fork crown mount, and a Radbot 1000 on their rack mount.

I do this w my gym clothes, 1 roll for lunchtime, 2nd roll for after work