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.