I'm guessing this question may be directed at least in part at me so I will fill you in on what I know. (Ironically I just had this exact conversation last night with another mom I know IRL...)
First - I don't recommend pushing for OOD prematurely. It's a big step that will cost the district big bucks so they won't entertain the request lightly. HK is correct - if your child is expensive or disruptive it will be easier. My DD was well behaved but I pushed and pushed not letting them off the hook as they screwed up so it ended up costing them as much to not meet her needs in her home school as it would cost them to meet her needs OOD. Same cost + meeting her needs + having me back off = an easy decision for them. Not sure how long it would have taken for a well behaved child without any of those 3 elements though.
Also as bad as our situation was it seems the horrible principal actually did us a favor in the long run. Her behavior was so egregious she really put the district in an indefensible position. The classroom teacher last year failed so completely in implementing the IEP it became very easy for us to show DD's needs were not being met in the home school. The district's total failure to follow through on the assistive technology also made it impossible to defend their position - they absolutely failed to provide a free and appropriate education.
One attorney I spoke to explained that generally speaking parents don't have a right to demand anything of their local public school - everything is up to the school board so parents have to go through them to effect any change. Parents with IEP's are the only ones who can make specific demands or have any hope of getting the district to pay for another setting. The bar to get them to do this, though, is pretty high. You can't just say you are not happy or want things done a different way. There has to be documentation that he has specific needs that are not being met. He is not entitled to a perfect education or even an outstanding education. He is entitled to an "appropriate" education. That is the important word to remember.
And also be careful about saying "no" things. This opens the door to them making the claim that you prevented all their attempts to provide this appropriate education. Our district's MO was to ask me how I wanted them to handle everything. And I mean everything. This put them in a position to say that anything and everything was being done according to the parents' request. Once I realized what they were doing I began responding by saying " You're the experts - I'm just a mom. You have been down this road before I haven't. What do YOU think you should do?" and then "You know - you're the ones with the federal mandate to provide an education. I'm just required to pay my taxes and present my child at the school house door. If you can't meet her needs in her local school it's up to YOU to find a way to meet those needs. Not me..."
My DD had an anxiety diagnosis and migraines that went off the charts when her needs were not being met so it was a pretty easy call in the end. The mom I talked to last night has a son whose behavior is spiraling to really bad levels so the district actually offered OOD. Even when it's a fairly easy call you still have to locate a school for him that will be able to meet his needs. That school also has to be willing to accept him and if you develop a reputation as a trouble maker the district could let potential placements know about this.
There's a lot to consider here. Hope this helped at least a little bit.
