When my friend Mrs. Bishop and I first received our 1:1 iPads, we encountered a problem we didn't realize we'd have: HEADPHONES! The (not great) cases that we ordered with our iPads made it very tricky to plug headphones in, and we could only use certain headphones with them. We thought buying better cases would solve our problem, but we still ran into the problem of kids coming to school either with no headphones, or with ones that didn't work great. Many brought $1 store headphones that broke quickly. Some brought headphones with the kids' auto volume control on it, so that they could hardly hear anything. Some were big and bulky, etc, etc. Headphones became a huge issue, not only for our iPads, but also using the computer lab for programs such as iRead. We needed a good solution.
We researched headphones and found these by Kidz Gear to be our favorites. They are sturdy and durable, but aren't huge and bulky. They retail for $19.99 on their website and at Amazon, but if you contact the company directly, you can arrange a bulk ordering price (I am not sure what the minimum # is, but Mrs. Bishop got her class set at a bulk price). This made them very affordable. Both Mrs. Bishop and I were able to purchase ours by approaching our PTAs for a grant. Some principals are also willing to purchase them for a class, and you can also try AdoptaClassroom.org or DonorsChoose.org for funding. They are totally worth it!
I give each of my kids a number and that is the iPad number they use, computer lab number they use, and headphone number they use. That way, if something happens to a set of headphones (or other equipment) I can approach that particular student and try to find out what happened. In the case of the headphones, we did have a couple instances of students intentionally ruining them (cutting the cords with scissors). In these cases, we talked to the parents and they were willing to replace them. I have since drafted a letter that will be sent home whenever a student "borrows" a set of headphones from my class set. That way, students and parents will know they are responsible for caring for the headphones. If you're interested in viewing the letter, you can find it here. You would need to do a bit of editing (I sent my letter home mid-year, when I received funding), but hopefully it will take away some of the work of starting from scratch.
Happy Teaching & Happy Tech-ing!