This has all the makings of a mess and I suspect that what the Americans call a satisficing solution will have to be found. This is based on the second best principle where there is no best likely outcome so whilst we can all expend sweat on seeking best outcomes these will not happen.
My best outcome would be that:
The Historic buildings were retained
The Covenant was honoured and the buildings used for Educational purposes
The Educational purpose of this school was in keeping with the Gove initiatives in England and some form of locally run structure emerged that would offer the very highest Educational possibilities in (say) the Arts, Science, Humanities, Sport, etc
That I had a job teaching History within the school (an ambition based upon the fact that I can’s get anywhere with applications for this type of job)
Once we all realise that we can’t get what we want, we need to focus on what it is that we least want and work backwards. For me, it’s the fear that these buildings which lend a real ambience to the town, will disappear. If the Covenant is solid, then I hope that some sort of Educational shuffle can take place, some less significant piece of space can be sold off and the site and buildings at least preserved.