Now that I have an easy-to-use tool for editing my blogroll, I've come to a somewhat startling realization. It's really difficult to decide what order the links should appear in! (I don't envy you, Dave!)
Now I'm not exactly a newbie at this website thing, which is part of why I was so surprised. Something changed in a big way since the last time I designed a set of navigation links that weren't solely utilitarian: There are a whole lot more things to link to. The last time I put any serious effort into a (somewhat) personal set of links was in late 1999, when I did the template for Jake's Brainpan. It's been a while. 
I started sorting things out about an hour ago. The important links floated to the top pretty quickly, but it steadily became more and more difficult to sort them. After all, what criteria should I use? Here are some thoughts I had about it:
1) How often do I visit the link? This is a very good gauge of how important the link is to me, but not very good for determining how important it might be to someone else.
2) How important is the site's author to me personally? Again, a very good indication for me, but not necessarily so useful to others. Also, the people who are really important to me might not update that often, so having the link near the top of the list might not even be that useful to me.
3) Am I an author or contributor? Obviously sites I maintain or contribute to should get some extra weight, but again, lots of sites I maintain don't get updated all that frequently (if at all), so how does that weigh in?
4) How often does the site get updated? This could easily be #1, but then I'd probably automate the order of the links (duh!).
5) How closely does the link relate to my work and my message? This is really difficult to evaluate, and may change from day to day more often than the previous four criteria.
So, I took a stab at it.
Number one has to be mom. No two ways about it, she's the most important person in my life besides myself, and even though her site ranks somewhat lower on the other four criteria, she gets the top link. Plus I like the way she writes. (Hi Mom!)
Number two is totally gratuitous. I'm the most important person in my life, so it only makes sense that I'd be near the top of my own links. Of course, I could have made this the first link, but something told me that the top link should be to someone else.
The next three links are to UserLand people. They had to be there considering how important UserLand is to me, and even though I visit Dave's site more than John's or Lawrence's, it made sense to group them together.
And this is where it gets fuzzy. The next 10 or so links are either ones I visit very often, or ones that I think are important for me, for my readers, for people who might be interested in the same things I'm interested in, or for other people that I link to.
After that it's a free-for-all. Most are people. Some are sites I have a hand in. Some are work-related, and some are not.
If you think you appear too far down on the list (Aaron ), please accept my sincere apologies regarding the nature of the printed word. It's not my fault that lists have an order, and that you can't be in two places at once..... (or can you?)
The conclusion I reached is that blogrolls absolutely beg for hierarchy. Imagine the following scenario:
Links organized into categories, with each link ranked (by order) within the category. Any link can appear in more than one category, with a different ranking depending upon your percieved relevance. Categories can be nested within one-another.
Mind-bomb #1: A category can be the blogroll from another of your sites.
Mind-bomb #2: A category can be the blogroll from anyone's site.
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