Any advice would be greatly appreciated!
I would lay down on my side with my arm that was on the bed extended at an angle over my head and baby, and I would usually feed off the boob closest to the bed, but sometimes the other too. It was DDs favorite position, and when she'd wake up in the middle of the night to nurse, I would just pull up my bra and get her latched and go back to sleep, and so would she when she was done :)
You might be able to try this: Lying on your side tuck your knees up almost like fetal position, prop your baby on your knees and nurse the breast not closest to the bed with the baby propped by your knees & against your belly. He will be semi sitting up, but it might work!
My daughter sleeps in a sidecarred crib. I have a "husband pillow" that allows me to sit up in bed. When she wants to nurse I prop myself up with that pillow, and then I can just reach out and get her, and when she is done put her back in her crib. I can sort of doze a little, but not sleep. (I haven't gotten the hang of side-lying nursing either... plus we have a small bed and there is limited real estate... but maybe I will figure it out at some point.) I am still awake for this process, but at least I don't have to get out of bed.
That alternate laying down position sounds interesting, i will have to try it! Maybe i just need to invest on a good pillow to use to get comfier in bed.