1. Can I import my current member directory (including members status, mailing address, expiry date, custom fields) into the system upon installation?
Yes. You can pass Custom Fields through the s2Member Import panel.
See: Knowledge Base » Import (or Mass Update) Users
2. Can I manually add people who join by snail mail and pay by cash/cheque, so that WordPress stores all my member info and expiration dates?
Yes. Just create the User, and set the End of Term (or date the User needs to be downgraded) manually through the WordPress Add/Edit User page.
3. Can fields be added to the database for members to complete when they subscribe eg: mailing address, phone number, interests?
s2Member provides this through Custom Registration/Profile Fields.
See: Dashboard -› s2Member® -› General Options -› Registration/Profile Fields
4. Can portions of a post be blocked so only members can see the full post, but non-members get teaser text?
You’ll need to use Shortcode Conditionals for this. You can find on those here:
Knowledge Base » Simple Shortcode Conditionals
5. Can I set up automated renewal reminders when members are about to expire? (I notice this wasn’t supported last June, any progress?)
s2Member doesn’t support it by default, but I posted an unofficial hack about how you might do this:
http://www.s2member.com/forums/topic/setting-up-eot-notifications/
6. We didn’t have an online subscription system before – Can I send an initial email to the whole database introducing the system and including their username and password?
s2Member imports Users silently, so that’s not something that s2Member’s going to do for you. You might could find a plugin capable of this, though. s2Member uses the default WordPress Users system, so any plugins you find on WordPress.org should work just fine. :-)
7. Mailchimp – Will the whole database go to mailchimp once I link the account? Do all fields go or just the name and email address? eg: their member status? Does their email disappear from MailChimp when they are no longer members?
s2Member’s User Import doesn’t add Users to MailChimp, as it runs silently. If you absolutely need this to happen, there are a few methods of stopping s2Member from running silently so your Users will get their information and be signed up to MailChimp on Import floating around the forums.