Hi J.,
I can completely understand! It's very tough to wean the extended nursing children. My daughter was so hard that I didn't wean her till she was 2.5 yrs old. Baically it comes down to the fact that it's going to be hard and you will probably not get very much sleep for a couple of days. When my daughter turned two I started to actively wean her. Before then I kept hoping that she would self wean. Some children won't so you need to cut them off. Sorry! I know it's hard because they get so much comfort from it but it needs to be done. Two years nursing is recommended length of time for WHO so he's coming close to the end anyway.
I started by cutting off all outside feedings. Then one feeding out of the remaining - upon waking, before nap or bedtime. The morning was the easiest. Rather than nurse her I would come into her room with some of her favorite food instead and we would have a little picnic after I changed her. She was determined to get the milk first but when I told her it was one or the other she still asked for mommys milk. Instead I gave her a bite of the food and once she got started she seemed to forget about it and continue eating.
Next I attempted to drop naptime feeding. She was waking at night up till she was about 21m then stopped for a while which eliminated that one. But around 2 she started waking up again and if she woke at night the only way I could get her down was to nurse. My peditrician suggested when she was 26m that she might not need the nap any longer which is why she is waking at night so I eliminated the nap which eliminated the naptime feeding. A real bummer since once she fell asleep she usually gave me 2hrs. Once I eliminated the nap it usually eliminated the night time wakening which left me with the last feeding - before bed. I did all this gradually since she was so attached and I also noticed that her behavior started to get more obnoxious. More like an ordinary 2yr old. Now that she's weaned the bad behavior - for her since she was pretty placid escalated. So prepare yourself. You're taking your childs pacifier away. My daughter never liked pacifiers either. She wanted the real deal and all the extra attention and touching that comes along with it. Prepare yourself for it but your child needs to become an independent person and you are doing the right thing even though when she's crying and looking heart broken it may seem like the wrong thing.
Ok, last feeding was the toughest and took the longest. First I went and bought her a really nice toy and said that this toy will be instead of the feeding. That didn't work she was hysterical and I gave in. Next, I bought her some really pretty pacifiers and a really fuzzy blanket and said she can snuggle with these instead. She was first enamored with the pacifier but when it came down to it she end up throwing it across the room. Screamming hysterically and I gave in. The last time I went and bought her a snuggle bug animal for her to whisper to and cuddle with at night. Like the bunny in Velvet Rabbit and that seemed to click with her. She still screammed but it wasn't so hard and she fell asleep after about 10m(if that) which I could stand. I also took her some where special that day so she could get a lot of running around in out doors so she was exhausted. I kept reading to her stories and bought some song books. Music seems to calm her and put her to sleep at times. It made the bedtime routine harder and I had to slowly bring that back down. I'm still working on that actually. One of these days I'm hoping that I can tuck her in and be able to leave but I still lay down on her big bed with her and sing with her till she falls asleep.
She still talks about mommy's milk and says she misses it three months after she's been weaned but it gets less and less over time. I try and sit down and cuddle with her some time during the day to make up for it.
About the clinging, I'd take him to one of those Kid's Day Out programs at the church. They're a wonderful way to slowly introduce your child to preschool or daycare. They're nonprofit so that the true spirit of making it a fun place for the children to come being the driving focus.
Good luck!!