Another toughie. I personally don't wake Olivia at all because I was taught (at sleep school) never wake a sleeping baby because they are sleeping because they need it and it is ever harder to settle an over tired baby. Olivia was a terrible night sleeper for weeks and then suddenly turned around one night and began sleeping for a few hours overnight.
With your little man still being only a few weeks old he still is learning day from night and is still needing heaps of feeds and sleeps. I know this probably isn't what you are wanting to hear because all i wanted too was Olivia to be settled overnight because I was exhausted but I promise it does get easier and they do begin to settle overnight.
Keep perserving and try to sleep as much as you can when your little man is asleep. Hoping he starts settling overnight for you.