My computer is in similar shape (purchased for school in summer 2008, currently on it's third operating system).
What has "solved" the issue that I care about is to pair down what data you are absolutely sure you need to keep.
For me it's Tax documents, budgeting spreadsheets and a password protected excel file that has just about every login/userid I've ever used (job hunting, one off websites etc).
Dropbox solved the issue. You get something like a free gig or so, and it integrates extremely well with windows. This allows me to keep local copies on my machine, but as long as you leave the "always sync" button on, it'll update continuously.