Not sure if S2Members will work for our club

Have a few questions about wether s2 is going to work for our club.
Currently running a Drupal Site with the following features. It’s a not for profit social club with a yearly memberships at $45AUD, with mostly older non technical members(Currently around 100 members). Paid Members can attend events run by the club.Currently members create events using a custom form, it is then “pending” until approved by a Activity Coordinator (who can edit all events). When approved the event author has full control of only their events… RSVP for events is required with reminders. We have a calendar view which shows all upcoming approved events, only visible to Members. Past events can be seen by non-members to show them the club activities. Recurring events are also needed, ie a regular weekly thank God its Friday walk, drinks. Excellent mobile support with iCal integration.It would be great if all the Member events could be synced with their mobile devices calendar etc. Even better if they could create events on their mobile devices and sync back (pending approval of course)
Every week a email newsletter is sent out with the upcoming activities. So nicely formatted and easy rich text emails is required. Currently we select the events that are going into next weeks Newsletter and click send and it goes out to all current paid members in a formatted email template.
We would like members to fill out a custom form before they join. We would like automatic email reminders when their membership is about to expire, say 1 month before, then 1 week before, then the day before. If the membership expires they automatically lose access to upcoming events and the newsletter. Currently members pay their dues by cash, check or EFT. Paypal would be nice. So manual approval of memberships is required
There are committee roles like secretary who have access to all membership details and others like treasurer or President who don’t. I would like to be able to assign multiple roles and permissions like I can in Drupal. Each year a new committee is voted in and they become responsible for running and maintaining the site. As webmaster I provide some help but basically we want a easy to run membership site with good support for a mostly non-technical people.
Basically Drupal is starting to act too weird and I’ve not used Wordpress in many years and I’m trying to get a sense of what’s possible with S2 and maybe other options out there. Happy to pay as well if we get good support for our members. Drupal has just been driving me nuts after using it for nearly a decade and I’m looking for a easier and/or more reliable option.