Long question(s): Looking for advice re plugins for various functionality

I’m working with some colleagues to build a website we can use with our existing coaching and consulting clients… and I’m realizing I could spend months just trying out plugins that come up in search results, so I’m hoping I can get some guidance regarding overall approach and some of the plugins I should consider to create an overall system that holds together well without a huge burden of ongoing administration.

The site is currently mostly to support the work we do with clients offline rather than being a self-signup/purchase and self-study type of programs site (although there will be some ‘standardized’ aspects that all clients in any specific program will engage). Eventually, we may also create some self-study programs that we open up for sale directly on the site, but that’s not a phase 1 launch requirement.

So, here’s my current list of the features and functionality we’re aiming for, and plugins I’ve either already settled on or have identified as potential candidates:

Membership system

  • need to be able to differentiate among clients based on what programs they’re taking with us.
  • WPMU Memberships 2 is a strong candidate

User profiles

  • would like to have an expanded user profile where we can gather info such as company, title, date of birth, etc
  • ideally with the ability to have emails sent automatically on birthdays, etc
  • it would also be cool if it integrated with some of the other functionality to have a sort of user dashboard showing upcoming appointments, completed assessments, etc. - perhaps via adding areas via shortcodes (maybe this is more of a view/template customization)

1:1 communications

  • ability for coach and client to communicate (private message or some such)
  • possibly an area where a coach can post info and/or questions for a specific client - different from a PM system in that it might integrate with other content, more like a comments system, but where only the coach and client could post and view the comments

“Course” type system

  • since there will be some standardization across our coaching and consulting engagements, it may work to organize content into “courses”
  • I’ve explored LMS systems, and they tend to be too pre-defined, and focused on courses where there’s some kind of measurement of completion, etc
  • ideally we’d like to be able to have automated emails going out to remind clients to access certain content, complete an assessment, etc.
  • ideally, this could integrate with an appointment scheduling system (although probably can manage if they aren’t integrated fully)
  • I think the “courses” idea of grouping content could be done just through the Membership plugin and setting access permissions
  • might be better to use something like CoursePress (I haven’t yet explored this)

Assessments system (for personality assessments, etc)

  • already set up using WATUPro, which works perfectly for creating the assessments and their score-based reports

Appointment scheduling system for clients to be able to set up their own appointments with their coach/consultant

  • ideally, we’d like something that integrates/syncs directly with an Exchange server, since that’s what we’re using for our calendaring — might be okay if it at least could sync by setting up a cron job to execute every hour or so
  • should have the ability to create custom confirmation and reminder emails that will go out automatically
  • ideally reminder emails can be customized based on the membership level — although could possibly be done based on appointment type (challenge is it puts burden on client to know what appointment type he/she needs to schedule — Program X Appointment 2 or Program X Final Appointment, etc) — I’m still thinking this through… I imagine what we come up with will depend on what’s possible with existing plugins

Custom content

  • Simply to help organize different content types (e.g., learning materials, assessments, coach tips, etc) I’m considering using a custom content plugin
  • currently exploring WPMU CustomPress

Right now, I’m still trying to codify or standardize on different client engagement types so that we can come up with a set of “groupings” of clients (since they need access to different materials)… it’s difficult to get into setting up some trial and error explorations of what will work - so, any suggestions that might help narrow down my search (or even let me know if something may not be possible) could really help.