ipMonitor definitely handles this scenario... and more... using the technique below:
My advice is to build a web page that does some app validity checking... and then output a specific value that indicates success. Have it be controlled via query strings (rather than post).
Next use an "HTML/ASP" or "HTTPS" Monitor to look for that value. If your web server tanks for any reason, the page won't emit the string we're looking for, the monitor fails, and then alerts will happen.
Now for the "and more part": Use this same method to check on whatever else in your environment that's custom not out-of-the-box supported from within your ASP page.