Where would you host the script? If it’s expected that the server that fires it off is always online and performing health checks, why not have it host a load-balancer? Or another local instance of the website? It’s something fun to play around with, but if this is for anything beyond a fun exercise there are much better ways to accomplish this.
Sounds about right. This keeps happening at my job, executives throwing good money after bad in an attempt to get some return on their investment. If we had just cut our losses years ago we’d be in a much better place now.