... FINALLY ...
So I finally did it. Amongst other things, forgetting that I should have copied my list of imagecache presets before embarking on such a journey. Everything seems to be in order so far. I did, unfortunately, break my "Cooliris Portfolio". Hoping to fix shortly.
The process is actually fairly painless on a small site like this one. However, I know there are some modules that don't necessarily follow a well-defined upgrade path. To note are the date module, cck, and imagecache.
I haven't looked into why but I got some errors trying to install the date module for D7.
With CCK, you don't lose any data, but you'll feel like you did for sure. If you have any cck fields added, just know that you'll need the D7 version of CCK and will need to enable, configure, and run the "Content Migrate" module from HERE. The claim is that it's still buggy with some CCK features - PHP generated allowed values comes to mind. - but I didn't have any problems at all (no I'm not using that particular feature).
Imagecache gave me no help at all. I had to wait until I got an error looking for specific presets. I took a screenshot of the list and recreated them in Media > Image Styles individually. Then applied them to the areas of the site that required them. That part really sucked. Print out all your Imagecache presets before you execute your upgrade. I'm sure there are other modules that you should have similar precautions for .. but this site is pretty simple so I had no other problems.
After this upgrade, I'm glad I don't have other very important stuff that needs to be upgraded. I will trash the data and start anew with Drupal 7.