He is about 6 months older then my youngest (nov 08). I personally wouldn't push it just yet. Iain is also very much a mummys boy & is only just now willing to go to DH if I say ask daddy. Things like needing help with the toilet or being picked up at the shops etc. For a loooong time it was only me. He would scream & carry on if DH tried. He would only accept me for anything! If I go out & leave him behind he cries. He gets over it pretty quick but he hates me leaving him behind.
I think he is finally letting go a bit as I have recently weaned him from the breast.

But no way would I try Day care yet. my DD started just last week at her new "preschool" (recently moved state) & Iain likes being there but would not handle me leaving him.

2 years is ages away as far as school goes. Yes he needs to start trusting others, but clearly he isn't ready yet. I believe he will be more trusting if he is allowed to be so in his own time. If it was me, I would probably leave it if its not a *need* to be in daycare & try again in 6 months. In the mean time, visit often, go to playgroups, visit friends etc. Get him socialising more while he is still in his comfort zone.