So is there any way to make sure the subsequent payment dates set up with paypal will be the expiry date rather than payment date?

No, What's been happening is members who pay after the initial expiry date, but still inside the grace period and then choose the auto-subscribe method of payment instead of pay now are seeing the next payment date as 1 year from when they paid instead of the expiry date of the plan.

From what I understand (and correct me if I'm incorrect), the next payment date will always be 1 year from the first payment date not the original expiry date.

What's happening:
Expiry Date: September 30, 2013
Payment date: October 23, 2012
Next payment date paypal will process: October 23, 2013

Ideally I'd like:
Expiry Date: September 30, 2012
Payment date: October 23, 2012
Next payment date paypal will process: September 30 2013

My guess is that its not possible, but s long as the grace period is long enough to take that payment on the 23rd the plan can renew. If this is the case, then I am probably best to NOT offer auto-subscribe beyond the grace period.

Hmmm, so if I switched the regular validity period to "This calendar year expiring 10-01" instead of 1 year would PayPal process the next payment from the expiry date no matter what date the initial renewal payment was made?

What happens to those members that have already renewed using the auto-renew option. What effect will changing the term do for them as all of the scheduled paypal payments will all be after the expiry date.

Also, not everyone is choosing the auto-renew option, so I have to be wary of how this would affect them as well.

Incidentally, I wished to go the route of this calendar year, but I've run into renewal date issues as outline in this post:

www.joomlapolis.com/forum/256-cbsubs-support/212448-understanding-qthis-calendar-yearq-setting?limit=6&start=6#212620

Until I resolve it, I can't go with that option. Hopefully you can shed some light on this