I want a guide to show on 2 different pages with different URLs. How should I set up the conditions?

When you create a URL matching condition you can use a regular expression.

To tell Guided Learning that the string is a regular expression surround it with square brackets [ ].

So, let's say you want your guide to display if either the word “homepage” or “adlist” appear in the URL.

The regular expression for that is homepage|adlist and with brackets [homepage|adlist]