Hi Megan.
1. Yes.
2. You can explain to them how to pay you by check, yes. Not sure what you mean by sign-up form to print. You can have the person register free and then upgrade his account manually after you get the check, though.
3. You’d create those separate access groups and then offer them to the user to purchase the one they way. You can use a separate button for each choice. You could customize the button’s code so the person can change the number of years.
4. No, s2Member doesn’t make this easy yet, we’re working on it. You could integrate with a service like AWeber or MailChimp and schedule emails to go out on those dates for now, though.
5. I don’t understand this one.
6. s2Member Pro has a User Export tool you can use for this. You can tell who’s expired by their user role, if they’re Subscriber/Level0, then he’s not a paid member, but if you allow free registrations then the role doesn’t tell if he was or wasn’t a paid member before. You can use the Notifications API to contact a custom script of yours that keeps track of members and their changes in status, too.
7. No, this isn’t possible with the current s2Member either. We’re working on making this possible too.
I don’t have a date for any of the features I mentioned being worked on, but I say it so you know we’re not ignoring those needs.
I hope that helps. :)