1. Lost/Stolen devices. Who pays for replacements? Why?
Did not happen to any degree (I don't recall hearing about any but it might have happened). The kids loved the laptops. They "grew up" and treated them as their most precious possession. We did not require them to take out insurance, just replaced from our stock.
2. Damaged systems that need replacement. Who pays? Why?
Happened very rarely. Couple of LCD screens got banged up (closing lid hard with pencil in the joint was the leading cause). Replaced the unit immediately (kid just exchanged at the repair room). We had a cheap source to replace the LCD (vendor set us up with their repair contractor). So no one paid anything.
3. Virus infections and such. What's the turn-around time on support for those? Will the school have extras to loan while they "clean" the students' machines?
Had Mac computers and no virus problems (don't hate me, it was true). We had replacements not loaners so all your data had to be on the server at all times. Any problem with the computer was dealt with by taking in the problem unit and replacing with one from stock. Then offline repairing the turned in unit.
4. Upgrade policy. Will the freshman class have better equipment than the senior class?
These started out as the units just replaced by a slightly faster model. Everyone in all classes got their computers from the same larger stock. All grades turned in their computers at year end and got a "different" unit the next year. But all the same model and style. For what you do with the laptop the fastest and latest is unnecessary. The plan was to replace them after three years with a new batch.
And so forth.
Throwing tech at a non-tech problem is stupid. And tech gets old really fast. And tech needs expensive support.
We had one adult in the exchange room during the day. The best techie student became the person that re-imaged devices (which was the first line of "repair"). And then any true damage was sent out for repair. 900 students with laptops. One person and a volunteer. The only crunch came before the year to image 900 units in a short period of time, but that is where we used adult volunteers and teaching staff in the summer for a week or so.
If anyone is truly interested I can share more details (I would need to look up some of the details, for example the number of extra computers we had in the tech room). Many parents were convinced their child could not be trusted (and many in the community were sure that these juvenile delinquents would immediately steal us blind). But other schools experiences mirrored what we saw. Very low incidents of any problems, these kids really rose to the occasion.
You're at Witt's End.