Quite understandable that your district would have to supply transportation to homeless students that reside in the district. But it sounds as if your district must supply transportation to homeless students who live out of the district. That does not seem right. In most places, you have to pay tuition if you attend school out of district. Now, excuse me while I put on my flame-proof suit.

Here's how I'm looking at this. There are three parties and their respective agents. One of these parties will have to pay for the glasses. 1) OP's DD. The broken glasses were hers. Without the proper glasses, she cannot see or learn. I will assume that she took the necessary precautions to ensure her glasses would not break in case of an accident. Her agent is her parents, who receive their funding through their occupations.. 2) The student who broke the glasses. Without knowing more about the child, I will refrain from giving him full blame. Although, he would have to be fairly high functioning in order for him to be going to school. His agent is his parents. I'm assuming they receive their funding through their occupations. 3) DD's 1 on 1. Her sole purpose is to ensure DD's safety on the bus (and that also includes the personal belongings). Unfortunately, in this instance, she failed. Her agent is the school district, who receive their funding through their taxpayers. And many taxpayers complain about being overtaxed to begin with. They don't want to spring the bill for somebody's glasses. IMHO, it's the school district's responsibility, being the agent of the 1 on 1 who neglected her duty. Fortunately, the school district has insurance. Hopefully, the insurance will pay for the glasses, and the district's premiums won't go up.