Regarding your first question. Yes. You can’t assign both fonts to same elements. So you need to remove from the top one and add it again.
However, this is not h4. MONDAY MORNING MULTI-LEVEL – IN STUDIO. This is h3. You need to check the element and not the class.
For this section Westshore Yoga 475 Royal Bay Drive, Victoria you need to use this custom css. .tribe-events-calendar-list__event-venue Please keep this in your custom element box and assign font to it. This should work.