Hello @kentjohnson4 ,
Regarding your questions:
This would depend on what product(s) you're pushing. If it's the same for each conference, then there's not really a need for multiple automations per conference, unless you're really wanting to maintain separate lists and automation reporting for each individual conference.
This would tie in with the point of question 1. If you're maintaining the same automation, like a welcome email or custom welcome path, then contacts already in the process won't be getting re-imported into the triggering list unless you've removed them from it prior.
As far as my recommendation for how to setup your automation, I'd do the following:
Create a list specifically for conference prospects, those people who have expressed interest in your product(s), but haven't actively agreed to working with a sales rep on finalizing a purchase. You could give it a really obvious name as well for the sake of quick identification, such as "Conference Prospect" or "Interested Buyers."
Create an automation path with a list-join trigger. Set the list to by the one made in Step 1. This way, whenever a contact is newly added to that list (aka they weren't already part of the list until they were manually added / imported as such), they'll begin the automation path.
Continue customizing your automation as desired, including conditional if available in your plan. Then activate the path. Now whenever you add a contact to the selected list - whether you manually added one you've previously uploaded, or import them from a source like a sign-up form or file upload - they'll start receiving those communications.
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