From my experience taking self-portraits while dressed, which is not insignificant, the real challenge is being able to take pictures while under pressure. I usually only have a few hours to dress and shoot, leaving precious little time to mess with photo gear, lighting, etc. I'm also worried about how I look, clothes, makeup, accessories, etc. I'm also always working alone. These are serious constraints to good photography. So the idea camera setup is whatever is EASIEST for you. One thing I've learned from this thread is that the wireless remote appears to be the killer device for crossdressing self-portraits.
As an example of how easy it is to screw things up while dressed, I made a video of myself last year attempting to take self portraits. You can see lots of errors in my approach--none of the shots came out. One thing I did do correctly is stand aside while pressing the button, to avoid messing up the autofocus
http://www.youtube.com/watch?v=PKkCHcQO0Nc