Thank you ladies. At least I know I'm not alone.
For the questions... I don't know whether he's teething or not. He acts like he is, but the ped checked his mouth 2 days ago and said no. Regardless, he's been getting a dose of Motrin every night before bed because he wouldn't go to sleep, shoving his hands in his mouth and wailing. Every night except tonight, that is, when he went down all on his own 2 hours before bedtime.
We were having a bit of a heat wave, so it was hot for a while, but now it's back to our normal chilly nights. Chilly enough that mommy needs a blanket. And he just sleeps in a dipe most of the time. I've been covering him with his fleece blanket, which seems to be enough for him (he runs hot). When it was hot, we were running a fan in the bedroom and he tolerates the white noise well, so I just keep it going, even if it is a bit too cold right now for it, really.
Bedtime - it's 8 now, although he went down at 6 today of his own volition. He wakes up like clockwork every morning between 6 and 6:30 (I'd much rather sleep until 8, and DH doesn't even get up for work until 7). I'm totally open to getting him to bed earlier. We'll see what time he gets up in the morning. The only real issue with that is that DH doesn't even get home until between 6 and 7, so if I put him down at 7, that means he sees daddy for maybe 30 minutes.
Positioning - he's in charge of that. He's mostly a tummy sleeper, but some nights he sleeps on knees and chest in that weird butt-in-the-air position. He's crawling, so he can get into whatever position he wants - which includes pulling himself up (to a stand) on the windowsill while still technically asleep.

If he falls asleep on the bottle, he'll flip himself over as soon as I take it away. If I have to swaddle or rock him down then I put him down on his side, but once he breaks the swaddle he'll usually roll onto his tummy. He only really sleeps on his back if he falls asleep that way and is just *out*.
The pillow - this is what I do before I go to bed, because otherwise I come in to find him smack in the middle (or worse - hanging off the edge). But it just doesn't seem practical during the night. He's against the wall, and I'm on the outside - DH sleeps in another room.
As for food intolerances, it is possible, although I haven't seen any regular signs of any until today (red butt today and red butt after introing bell pepper a couple weeks ago). But it is odd since I didn't introduce anything today. I'll go back to basics tomorrow and see if it clears up.
And I think tomorrow DH will be sleeping with the babe. He won't/can't do it during the week, since he has trouble getting back to sleep after each waking, but he's willing on the weekends. I just haven't pushed for it.
I'm going to try to keep track of how many times he wakes tonight... I've been so exhausted lately that I can't remember in the morning.