Some Thinking out Loud

I am used to having diametrically opposed impulses. I’m a pack rat! But I love order and cleanliness and organization! I’m lazy! But I want to do everything in the world! Etc.
As occasionally happens for me, now I’m having diametrically opposed impulses around my website. On the one hand, I hate it when sites I like go away, and so I want to have every page I ever built, ever stay online. On the other hand, I want my website to actually, yanno, reflect me as I am now. I’ve tried to halfass it by leaving sites up in archives or whatever, but I still get email about them from time to time (mostly the Lorre Library of Sound) and then I feel guilty for not keeping them updated. I want to take ’em down rather than halfass it. I want to do an enormous redesign of ealasaid.com and have it be awesome and coherent and cohesive.
But then I think, what about the people who like those sites?
ARGH.
I am currently dithering over a handful of options.

1. Find someone to take over The Lorre Library and A Special Kind of Person and the others so they’re still out there, just not my job and not on ealasaid.com.
2. Just delete the sites I don’t want to deal with and remake ealasaid.com. If they want to see the old sites, they can look on Archive.org
3. Delete some of the stuff and make a concerted effort to update the rest of it as part of the new, improved ealasaid.com

I’m leaning toward the last one. Since I started learning Joomla for Californiabats.com, I’ve kind of fallen in love with the simplicity of using a content management system. I like how easy it is to add menu items and move things around and so on! It’s awesome! It’d be pretty straightforward, I think, to use Joomla or MovableType or something similar for ealasaid.com in its entirety. It’d sure make updating stuff easier. Hell, I could use Joomla for the static stuff like my fiction and columns and reviews and keep using MovableType for my blogs. Even easier!
I’d be interested to hear the thoughts of my readers on this stuff. How do you decide what to keep and what to get rid of on content collections you maintain?