You're clearly in a very difficult situation. I completely agree with you on the hobgoblin of little minds, and yet, getting your DS to accept challenge and stick at things has been a recurring theme in your thoughts so it's clear that you agree your DH has a point there. In the end, perhaps the fact that he feels strongly that your DS should stay where he is and you're on the fence answers the question...
Here's what I'd do, if it were me, fwiw. I'd give the private school their $400 deposit, and I'd be quite open with them that DS probably wasn't coming. The way I'd look at it would be that this was an insurance policy, but, unlike most insurance policies which just bolster some multinational's profits if you end up not drawing on it, this one might end up being a donation to a worthy cause, and how bad would that be? (You might be able to get the school to agree that this would count as your deposit in the future if you end up moving your DS to them in some later year, or you might not: point is, although it's a lot of money, in the grand scheme of things, it isn't, and sometimes it pays to think that way.) Then I'd carry on with the working assumption that DS was staying at the Montessori for now. I would, however, resist making a financial commitment to them until I'd seen some definite improvement in DS's happiness there, or at least convinced myself that it was definitely right for him for now. If pushed, I'd probably say "if we have to make a firm decision right now it'll be to remove him, but we'd rather work with you so that we don't have to...".
What I'm less sure about is how I'd present this to DS, and even if I knew obviously YMMV! I think, would be that I'd explain to him that my concern was that I thought part of his problem with the Montessori school was that he wasn't buckling down consistently enough and working hard. I'd tell him that learning to do that was so important that there'd be no way I'd move him again without him having learned that - so that, *if* by the end of the year his Montessori teacher said he was working hard consistently, but he'd still prefer to switch to the other school, then that'd be what we'd do, but that if he wasn't, he wouldn't get that choice. [ETA: actually, this isn't entirely consistent with what I said about - you see, I do get that it's difficult ;-)] At the same time, I'd really emphasise that nobody expected him to get to perfection in one leap, and I might help him with the negotiation on how much he needed to write.
Another point I might make is that a highly flexible, small class situation can really only work if all the people involved are committed to working hard and making it work - small classes are great, but it only takes one non-cooperative child to make it impossible. So even if you decided now he was going there, he really would still have to learn the sticktoitiveness: you wouldn't be lying to him in saying this, I think.
Good luck!
Last edited by ColinsMum; 01/24/10 09:08 AM.