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Great question. An answer here will be working off some assumptions but I think this can be addressed fairly directly.
If Capsule knows the listing type as fed from your site and it has the email address you're looking to mail with you'd want to build a report to output each of those variables. Difficulty level... probably 6/10 for most CRM users.
Once the reports are built they would dump to a CSV table(s). These could be batched and identified by a keycode given to Mailchimp or you could upload them to X number of different individual campaigns.
Depending on the frequency you need this process to occur you could probably do an API with Mailchimp and feed this same information to the same places though I'd expect to pay for it. The CSV dump is way more practical for most applications though, especially if you aren't updating your mailing file in real time.
We deal with stuff like this all the time for clients - if I can help with specific process design let's set up a call.
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