Years ago I put all my data on Dropbox, including logons. Changing computers is never any fun, but my basic, use them all the time programs are pretty easy to reinstall. Also, I love Office 2003, the last really great suite before they went retrograde and put in the Ribbon (emulates the 1980s Wordperfect and Wordstar menus but with excessive mouse clicks) and changed the default format. Drop down menus are by far a better solution for us. I purchased about 36 licenses for it and still have half of them left, so I don't have to recover and reinstall. Works fine in 10, which is a better OS by far than 8.
Most of the time the problem is a bad hard drive or power supply capacitors that have dried or burned out. I've kept a reliable XP running for years by replacing the power supply and installing cloned disks. I always keep the most recent old disk just in case. You can't clone a dead disk.
Security isn't much of an issue, but I recently found I could buy 10 licenses for Norton Security for $100 bucks a year, and it's pretty darn good, Even on my older machines, never a virus.
Another good app to add is email and browser backup called MozBackup. Freeware. It will preserve settings and logons, so keep a copy somewhere safe.
And welcome back, I recall you being pretty with it on woodworking stuff.
The more I do, the less I accomplish.