I am making a proxy site & have been advised to keep the word 'proxy' out of the name as this can trigger an automated filter block. How do most school boards block proxies? Do they block by IP or domain name? If a proxy shares an IP with un-related legitimate sites do all get banned? Do they have automated filters based on keywords or is it a manual site-by-site process? At the local high school it is up to the overworked network admin at each school to manually set blocks. There is no overall school board co-ordination or block.
Also if students use a site a lot they will probably investigate the site to see if it's a video site, game site, proxy site, etc.
It really depends on how active your firewall runner's are. They might never check or look at what's going on and you could be fine. Some check for certain things in the HTML like a known form of PHP or CGI proxy. The domain will probably blocked if you get it listed at proxy.org, too.