Congrats on your initiative and resolve! This website has proven invaluable to increasing my enjoyment and safety when commuting. It sounds like you've done everything right, especially giving yourself more time than needed so you can go as slow as you need to be safe in traffic. While fitting the stock wheels may be an admirable goal, you can't beat the reliability of slightly overbuilt components. I have bike commuted regularly for 23 years, primarily for fitness, so a little extra weight here and there in exchange for reliability, comfort or utility doesn't bother me. And as far as those head winds. I'd like to say there will be an even amount of tail winds, but that never seems to be the case. But when the wind is blowing in your favor....there is nothing better!