Nesting Scheduler under RiSE site

I'm trying to 'nest' the scheduler as an application under a separate site in IIS. I'm pretty sure this is what ASI hosting does for the cloud clients. I'm looking to set up www.abc.org/API to get to REST API for a 20.2.26 (2015 Q4) client, who does not have a wildcard cert or a unique subdomain for the default site in IIS.

running into duplicate connectionStrings error and when I try to <clear /> prior, I get invalid web.config because of a missing section declaration (different sections based on where I tried to place the <clear />).

I've tried to the data source, but get "The section is marked as being protected, but it does not have the correct format. It should contain only the <EncryptedData> child node."

Any suggestions?