jadedmoonbeam!
I totally overthink things (just ask my BF!) and am huge on the list-making. Like you did during the massage, it's good to try to focus to keeping your mind in the present. I rarely have trouble falling asleep (and don't have tv, so that's not an issue), but know what you mean about waking up to thoughts whirling around and not being able to continue sleep.
Again, like during the massage, having to keep bringing yourself into the present can take some doing. It's not as if you can tell yourself once and voila! It takes practice, and that's ok.
Hope your visit with your T goes well. Keep us posted, ok?