Oh Boomba
Wish we lived close by, you could join my group of extremely relaxed mothers. I think you'd fit it perfectly

I'm not looking forward to the day my DD goes to kindy either
She is like your DS, always asking when she will be going to school. The other day I told her when she goes to school, I'll be sad and miss her lots. Her response, "and I'll say, Its okay mummy, I'm just going to school!" heehee. When they're ready, they're ready! If you decide to go through with it, make sure you're both comfortable. Find one perfect for you both! Don't feel pressured to do what others are doing, you are his mother, do what you want, and what you feel is best.
xo