Dave: When people think of the UPA website I want them to feel impressed. Right now the site does not have much of a welcoming feel, many things are hard to find, and there is not much to regularly bring visitors back to the site. Even though there is a wealth of information and functionality on the site, the experience of using the site isn't very smooth.
In designing a new online presence I would first focus on fixing what's already there. First, there has to be a better way of presenting the massive amount of information that upa.org contains. Even though I visit the site all the time, I still find it hard to find certain items. I do not know exactly what the breakdown would be, but I would like to work with a group of people to come up with something new.
Second, as the UPA is already doing, I would like to examine the online rostering system. Don't get me wrong, I actually really like the existing system, but there are lots of people out there that have problems with it all the time. I think a big part of those problems have to do with people not being familiar with how the system works, but there may be a way to smooth the whole system out some more.
Third, I would like UPA.org to be a forge that brings together all of the various sources of Ultimate information. For example there is the tournament list
right here and the RRI tournament list
right here. Then there are the tournaments that are just listed on RSD. I want the UPA.org to host the be all end all tournament/event list that is actively populated by many people.
Fourth, I want there to be more of a reason for people to come back to the site. I want to see a massive media gallery built in to upa.org -- Something like a free version of UltiVillage along with a spectacularly huge image gallery. Along the lines of having a reason to come back, I want the UPA to host it's own forums. I love how each ultimate community has its own forum, but I want the upa to host the most active one, or at least one that can replace the need for my favorite (sarcasm) all-time repository of Ultimate knowledge -- RSD. Right now upa.org is mainly just a basic information site -- it has deep info, but nothing interactive. I want fresh content. I want the UPA magazine published online.
Lastly -- and this relates to many of the points above -- I want the site to look nice. I want clean, simply, and utilitarian.
These are not easy things to change -- They will require money, and that's one thing Ultimate players have a weird view on. How many times have yo heard something like, "I want the UPA to do this, and this, or this, or this." right along with, "Why they heck are they charging me $40!".
Note: I do realize that people have very legitimate reasons for not liking the membership fees, but that's another issue that I'd be happy to address if someone would like me to.
All I'm talking about is... a better web presence is going to required a solid amount of cold hard cash. It cannot be another volunteer project. What's online now, while functional, is undocumented, unscalable, and unstable. A system needs to be designed that can handle the continued growth of the sport.