I second the cold turkey approach. At this point, your baby is old enough to be taught how to fall asleep on his own, and for the cry it out method if you are ok doing that. In terms of getting babies to sleep, many parents fall into either the attachment parenting/co-sleeping (Sears) camp or the cry it out (Ferber/Weisbluth) camp.
We did cry it out so I'll elaborate on that. This will cause an uproar with some moms who are against this approach but it's only one possible method out of many and it worked for us. It's from the Richard Ferber book "Solve Your Child's Sleep Problems", he is a doctor, not a pediatrician but a sleep expert. Yes, he gets a bad rap but mostly from people who haven't read the book and don't know the extent of his expertise on the subject of sleep. According to Ferber, we all wake up multiple times during the night, it's just the natural way our sleep cycles occur. Adults don't even realize they've woken up and just go right back to sleep, but babies need help falling back asleep because they are not used to this. The Ferber method teaches babies to fall back to sleep on their own by crying it out if they need to, but you don't just leave your baby to cry indefinitely - you check on him periodically so he knows you haven't abandoned him. You just can't pick him up because then he learns that crying gets him picked up. It's hard and it's not for everyone. If you'd rather do the co-sleeping thing, you could bring your little guy into bed with you and he'd probably love that. You just have to be careful with all your pillows and covers. But my friend has a 2 year old who's used to sleeping in her parents' bed, and now they can't get her into her own bed.
From what I understand, the Weisbluth book is similar to Ferber. If you decide to let your baby cry it out, read the book first and expect the first few nights to be tough. If you follow it exactly as outlined, it works. We let our daughter cry it out at 9 months old and after 3 horrible nights (I cried too), she learned to fall asleep by herself and has been sleeping through the night ever since. A lot of moms on Mamasource are against the "Babywise" book because the author has no medical background and makes unsubstantiated claims.
Also, we've all heard it's best to put babies to sleep on their backs, but if yours has good head control and can roll over freely, I wouldn't worry about him rolling onto his tummy. Lots of babies sleep better on their stomachs, mine does. If you're really worried, you can get the Angelcare baby monitor, which has a motion sensor and will sound an alarm if your baby stops moving or breathing for more than 20 seconds.
A lot of babies rub their fists in their eyes, it's just the age. The best we can do is keep their nails short and filed to minimize the scratching, and wash their hands especially before bed.
You probably want to get your son into a sleep sack or a blanket sleeper (footie). I really liked the Cloud B Lullabag, but for bigger babies the only brand I know of is Halo. They come in lightweight cotton or fleece.
BTW, Swaddle Designs makes nice big flannel receiving blankets that are about 42" square, enough to hold larger babies. They're pretty pricey at about $24 but probably the biggest on the market and really good quality.
Good luck and let me know if you have any questions about anything I've said.