Breaking my heart

Today I decided it was time to confront Jacob's current state of mind. He has been pleading a sore tummy for days, and has actually manifested some physical signs of illness, ie. many trips to the bathroom every day.
After some suspicious behaviour and a few comments from him about school, we decided this must be an anxiety based condition. Since mid-July, when we started talking about school approaching, he has been less and less interested in going to friends houses or going anywhere without me. Things have been getting worse and worse with his reluctance to be without me, or to branch out at all.
Today we forced him to go out, go to swimming class and go to see his old friends. The trip to swimming class started badly, with many tears and protests and lots of complaints about being 'too sick' to go in the pool. We took each step one at a time, in the locker room, into the swimsuit, feet in the pool....then finally, in. And he loved it, as he always does.
After swimming, we stared prepping for the trip to a friend's house. He immediately started complaining about being too sick to go. I told him he was going regardless, and if he was too sick after we had been there for 15 minutes, then we could go. Right up to the time we walked in the door, he was 'too sick' to go and had to be repeatedly assured I was staying the whole time. 30 seconds after we walked in, he was playing and totally forgot to be sick. Still had 3 trips to the bathroom while we were there, but said he finally didn't feel sick anymore!
Once we were home, he started to complain about being sick again. I've been trying to figure out for days how to reach him and find out what's the cause of all this. Finally, after supper, out of the blue, he says "It's not fine at Crane."
So I, with a little prayer skyward for the right words, asked why.
He crawled onto my lap and buried his head in the arm of the couch. He said he didn't want to tell me why. I suggested a number of options; is it scary? Is there a mean kid? Is the teacher not nice? All were met with silence.
I asked if it was because he missed his friends, and he lifted his head an inch. I asked if he was lonely. He looked up at me with teary eyes and said yes. Oh, my poor shattered heart. How do I fix that?????
I offered all the platitudes I had for a sad little 5 year old, and promised things would get better after he got to know a couple of kids. And in my head, I know they will be better. He is a popular kid at daycare, and I know he will make friends as soon as he's comfortable enough to do so. But until then, every day I will send him off in the morning with a little piece of my heart coming loose.
And now I question every decision I made that has brought us to this point. Should I have pushed so hard to get him into the French Immersion school, when his best friends went off to English schools and left him alone? Should I have kept him at his current daycare or tried to get into the daycare in the school, so he could be developing relationships with classmates more quickly? Can I quit my job and stay with him 24/7? Can I build a little bubble that bad feelings cannot penetrate and keep him in it forever?
Oy. I'm so sad for my little sweet baby boy, who is being forced into a world he doesn't yet want to be a part of. Will he ever be excited to face a new challenge? Will I ever be ready to let him?

**update**
Today was the worst its ever been. Jacob refused to stay at daycare and had to be held there while Pete left. When it was time to get on the bus, he sat down in the hallway and started bawling. The teachers couldn't get him on the bus no matter what they tried, and I ended up leaving work and going back to the daycare to drive him to school. Let's just say that 45 minutes of my life is best left on the floor of the kindergarten classroom where it took place. My red, swollen eyes are a testament to my day today.
I got all kinds of phone calls from the teacher and the daycare to reassure me, and finally a call from the daycare director. Apparently Jacob had a great time at school and was happy as a clam when he got back to daycare. They did discover, after much prodding, that the issue is with the bus ride to school, not school itself. Jacob has been getting teased on the bus with some regularity, apparently.
(insert insane feelings of rage here).
I'm told there was a reckoning when the older kids got back to daycare today, the teacher tore into them all, and threatened them with suspension from the bus. Her anger was almost enough to put a dent in my own feelings of rage. One of the students drew a picture of her, depicting her feelings of anger. They made all her hair stand straight up off her head. It was quite comical, and a pretty accurate depiction of how I felt!
On the ride home Jacob admitted that all his bad feelings about school are due to the bus ride. He has given me so many different reasons now, I can't be sure this is the only one, but it does seem to be a big one. He did say he wants to go to school, but he wants me to drive him there.
I've decided to stake out the parking lot tomorrow, and watch him get on the bus, so I can be there to encourage (or push, as needed) him onto the bus.
Damn, life is hard!~
Still, a blessing in it all? I have somehow found a mama bear daycare teacher who loves my kids, a teacher who is willing to go the extra mile, a daycare director who is not afraid to stand up to parents and kids alike, and a husband who knows how to make me smile through the tears. I am blessed not to be alone in this.