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The fact that there can be several attachments on a card, human intervention is generally required even when using Power Ups to handle this requirement.
I have worked with several but I have yet been able to locate one that allows you to select as part of an Trello automation process. This is in fact requirement from one of my clients.
Power Up (third party) data is typically not available to Trello automation but can be accessible if they are written out to something like a custom field, card description .. or have api that allows you to access the power up data and you can use http request to get them into your automation.
Trello automation for email, as far as I am aware, does not allow you to attach any file(s). I have not come across Email Power Up that does it. Having said this attaching the first or last (without having to select) is doable as long as you can deploy an proxy to get the file from the card.
Yes, I have been able to create a list all attachments. When user clicks on any of them it will activate a download or show the file because the link is to a microservice that will handle it for you.