I managed to get a copy of all my old blog posts today, so I'll be able to restore some posts at least as old as 2002, there may be older but I didn't have a chance to check how far back the history goes.
I spoke to an advisor at Clark College today, pretty much told me what I had already anticipated, that I should start off slow and take the basic prerequisites before moving forward, and he recommends I start the math track because it's long.
I'm going to do a little more CrowdCompass work, and then I'll take a small excursion to try to get textile or markdown working on my blog posts, maybe I'll tell you guys about how that goes next if it isn't too embarrassing.
P.S. - I got markdown working with Redcarpet ;-)