how is going thru DSS and being on the trail as a SGT E-5?

It's not any different from being an E6 or 7. You're all going through the same thing and you're all NCOs, and you're all playing the game. Once you're on the trail there's almost no difference in rank between the drills. You're all looking out for one another. That's been my experience at least.

As already stated, you're an NCO and treated as such. Just remember be professional and pay attention to how you do things. Also remember once you get out and start on the trail, you will develop your own teaching style. Going through school is lots of memory work. It's important to get things right, and no matter what rank you are, it's the same process. As a SGT I do feel you do have an advantage - when it comes to promotion you will have a little step up because of the course.

You are peers by job position only. Rank, customs and courtesies, and military bearing still apply. You are setting the example not just for young soldiers but for civilians that want to be soldiers. That said, I have great working relationships with the Sgt DS'S that I work with. I have worked with SGT'S that have a chip on their shoulder cause they were the lowest ranking and no one likes to have to pull rank on fellow drill sergeants but it'll happen if you're that guy. So be positive and do the job. Play the game so to speak.