My last question should have asked if there is any downside to setting the timeout quite high, I don't want the IIS Server to shutdown the process after 2 minutes. I'm wondering if I should set it to one hour. Another thought is to set a timer on a workstation to call the app every 15 minutes and leave the setting at 20 minutes. I could return this to a log and send a message if there is no response. That seems like a better solution, what are your thoughts? I could use the Task Scheduler on the machine (not the server but an external workstation) to run the 15-minute server test starting one hour before business hours and ending one hour after normal business hours.

There's no reason to have IIS shut down on idle so you can set this at a high value. It saves resources but if your app is the only thing running there's no benefit for that. This is mostly for bigger organizations that run many Websites and want to save resources.
+++ Rick ---