I can't even get my Howlingmoon to fold up completely with my sleeping bags in, let alone my annex. (That said I have not climbed up on it when I fold it up either).
I leave my two 0 degree sleeping bags (Wiggy’s, love them!) that are zipped together up in my Howling Moon 1.4 Tourer tent along with PJ’s for the kids & me. The only thing I carry up before being able to get in bed is the pillows & a fresh change of clothes. I do have my rainfly completely removed which did add some room for closing. With the fly off I can actually see the stars through the stargazer and haven’t had an issue with water getting in, although I’ve only had it in the rain without the fly a couple of times.