I also have a friend who works for SW. I have used many buddy passes over the years and have not had any problem using them even during peak travel times. You just have to be flexible. One very nice thing about them is that you can use non published routings to get where you want to go. Just pick up a flight schedule, study the nonstop flights from city to city and you can find some interesting ways to get where you want to go. Sometimes you can catch a flight that would not be an allowed connection if you can get off the plane in time and make it to the next gate before they close the door. An early arriving flight helps and I have had it happen a few times. It helps to have a back up routing or two in case you can't get on one of your planned flights. There is a toll free # you call to make a booking and they will tell you what the loads look like. I usually check them a week out, then 2-3 days out, then the day before, and the day of travel. I have found it best to not check a bag if traveling during peak times since you may not know until the last minute whether you will be able to get on one or more of your flights. Another thing I have done is use 1/2 of a buddy pass and 1/2 of a RR ticket if there is a flight outbound or return that you need to have confirmed. I don't remember a dress code other than clothes in good condition and clean.
Dan