I wish I had written what I did down cos now that no.2 is coming I am scared I won't know what to do!! But anyway...
I would leave him swaddled if that usually helps him sleep. I weaned my DS off the swaddled towards 4-5 months but was doing dreamfeed from around 10 weeks. Keep him swaddled as you do the feed too unless you need to undo it for BF positioning. No need to wind apparently as they don't gulp as much air when they are sleepy but I think I may have held DS upright for a short time afterwards as he easily brought up wind usually.
I usually did the feed between 10 and 10.30pm. I think some of the so called baby gurus recommend not later than 11 and not earlier than 10 but not sure of their reasoning as I only ever borrowed books from library...
I dropped the dreamfeed by around 5-6 months (and he had started some early solids) - just went cold turkey one night after talking about dropping it for ages. One night I was just so tired and I couldn't muster up the energy!! He didn't miss it which was great!
There are 2 schools of thought on the dreamfeed - some say to keep the baby fast asleep and others say to rouse them so that they are in fact awake (but is that really a dream feed then??? not sure). I did a bit of both as sometimes he woke anyway before I went in or as I was doing it. To be honest, I don't think it really made a massive difference if he woke or not - though I had to switch to a bottle and I know that if he was fully awake then he took less milk which may have led to another waking later on but if he was sound asleep then he just kept drinking and drinking!
I would give it a week before deciding if it is doing what you are aiming for - some babies are actually more unsettled by doing it as you interrupt their natural sleep pattern and I have read that doing it for too long can also have that affect (by too long I mean beyond a certain age....but don't ask me what that is!! - like I said, I wish I had made more notes on all this first time around!!)
Hope that helps. I will look forward to hearing what others have to say and then I will save the answers for my no.2!