So, let me try to deconstruct... policy is that the PR Director is the primary person in charge. Is it true?

It is one of the duties of the PR Director, based on advertisements for the position.

I wonder then if it was so for the previous PR Director and, if so, whether indeed, she was truly able to access the areas that needed work or whether there was shared responsibility -- i.e., various departments being responsible for their parts of the Web site, which is often the case.  For instance, she might have had resonsibility as the "Managing Editor" but no accompanying authority to incent others to take care of their screens.  That might make it difficult for someone to be successful.

The site should allow us to pay assessments, pay any fees (golf, swim, beach, etc.),

Certainly possible. However, in my view this aspect is highly overrated and I'm not convinced the benefits outweigh the costs and troubles involved. It would also require complete integration with OPA's existing membership database and potentially expose that to some risk. Doing so would require security at a level similar to what banks employ.

It can be outsourced; however, you're probably right about the business need not being there -- especially if few people use the site or know about it.  Certainly quick and easy access to info, easy navigation and a more intuitive UI ity is first priority.

My brothers and I (all of whom are well versed in the use of the Web for community resident use and/marketing... my brother runs several community sites)

Perhaps your family would be interested in handling the OPA web site.

Oh, no...    I only mentioned our individual experiences in order to demonstrate that I understand Web sites (content, back end and user interactivity) as does my brother even more directly where this type of site is concerned.   

From my own work I know it is very difficult for non-profits especially, but even for for-profits to arrive at the right design, the right functionality and the right people (or ways to train people) to maintain the site.  A reason why there is so much outsourcing. 

As I'm sure you know, the initial discussions about concepts can eat up a lot of the budget. 

I've found that in many non-profit and even for profit organizations people aren't always aware or experienced enough to understand what it takes -- skill sets and even internal organization support -- to keep it running. 

It's not an easy thing in the first place, so inheriting a difficult system can be a nightmare.