Hi L.
Here is my experience. I just weaned my daughter about two weeks ago and I did it sooo slowly.. She will be 17 mos next week... After she turned a year I stopped pumping at work and over a few weeks cut out the feedings except for morning, naps and bedtime.. I can't remember when exactly I cut out middle of the night feedings but it was sometime around then, I just stopped offering and instead just rocked her... I slowly cut out morning and naptime feedings, morning seemed to go faster (she wakes up around 6) I would either just get up and start the day and bring her down to breakfast, or if I wanted to rest a little longer I put in a dvd and let her watch in bed.. Some days I would still feed her if she wanted it, but most of the time the dvd distracted her enough.. Naps were a little harder. I would try to not feed her and just rock her, but if she got upset I would then feed her.. If I had errands I would try to time them so we'd be on our way home around nap time and then she would fall asleep in the car... I guess by about 14/15 mos she was down to just night time.. Gradually, I just cut back the time I was nursing her at night from about 15 mins to about 5.. When she was just on bedtime, occasionally she would ask for it in the morn. or naptime and I would tell her no milk, just at bedtime. I also had my husband put her to bed once in a while... Two weeks ago when I weaned her I just had my husband do bedtime by himself for about 4 or 5 nights in a row. We skip the milk at bedtime and she is fine. Then I did bedtime, and she went to sleep without milk.. Then the next night she was upset so I let her nurse and after about 2 minutes she pulled herself off and has not asked for it since...
I really think its a "two step forward, one step back" process..Also it takes some trial and error to see what works for you. My daughter eats dinner around 530-6, and is in bed between 7-730.. She usually wakes up by 6 or 630 and I shower and get dressed and get her dressed and bring her down to breakfast..
Maybe have your husband go into him at 5am and comfort him and see how that works.. Or if you want, offer him milk or water first and see if he will take it.. If you can, I think you should not give yourself a time limit of 4 weeks. I think that might put too much pressure on yourself and make everyone frustrated.. I think its ok to cut out a feeding and then if you have a day or a few days where he needs that feeding than give it to him. Then try again the next day.
I was so anxious about the whole weaning thing, but found that once i relaxed about it and just let things happen it worked out fine.. I just decided to take my time and try to wean while keeping her happy and content and not turning it into a battle.
Good luck!