Documentation on highrise interoperability a little lacking?

Hello, I'm trying to implement a solution between highrise/mailchimp and I've been running into all sorts of problems.

The primary problem is that I would like to import all of my highrise contacts into 1 list, however, I need certain tags to be imported from highrise and show up as groups within mailchimp for segmentation purposes. Otherwise, I am going to have to use mailchimp's import via tag and create 4 separate lists, largely of identical people, which counts against my monthly totals.

The second problem I am running into is, if someone opts into my mailchimp mailing lists (via something like the wordpress plugin), will this create a new contact in highrise? Specifically, will it add them when they opt in, or will it add them once I send an e-mail to them as long as I have the "Track Member Activity" option checked?

Thanks in advance,

Andrew