Your going to get tons of advice from all angles. Just go with it. You'll figure it out. Look at what other people are doing and change if you think it will work out for you. You will be surprised by the number of people that spend no time preparing, figure it out as they go, and make it the whole way. Tons of places in the South to re-outfit yourself. Starting in the south in peak season is a really forgiving time and place to start.
My only other advice is if something hurts or feels wrong, then there is probably something you can change to make it feel better.