If you walk from waiting room, to office with T

I get walked from the waiting room to his office usually I walk behind till he opens his door then I walk past him to get to the couch. He usually leads me out and watches me leave.

This was actually weird to me at first mostly due to the fact last time I went to therapy I had to check in with a receptionist and let myself into the therapist's office.

I like the idea of being 'welcomed' and only having to interact with my T while there, it's quite nice.

Not awkward. It's a similar setup to the new office you described and my T's office is the furthest from the waiting area. She usually asks me about either my drive(it's an hour) or school/classes. So casual talk until the door shuts.