A couple days ago, I tried cloning my Windows Vista drive in preparation for upgrading to Windows 7. Something went wrong though, and my original drive wouldn’t boot anymore because of the infamous winload.exe. So I got rushed into upgrading to Windows 7 earlier and unprepared. But luckily, to a large degree I was prepared:
1) Maintain plenty of free space. I did a fresh install of Windows 7 on my old Windows Vista drive. The installer moved all my old users, documents, programs, and system directories into a safe place so you won’t get anymore strangely named system folders like Windows.1 anymore. Because I had plenty of space, I could just move my old files instead of going to a slower external backup.
2) FireFox. To get FireFox up and running, all you need to do is install it, then move your old profile to the new. You have to make sure you get both the Local and Roaming data, and Google Gears is an external install that won’t transfer along. If you can’t do that, use Weave, which will sync your bookmarks, passwords, history, etc. This trick will work for the majority of the programs you use. Step 1) Install a program. Step 2) copy old profile data over.
3) DropBox. I keep small useful files, and small portable apps in my DropBox. That means I have a lot of functionality the moment my DropBox is synced. You should grab the 0.7 betas from the forums instead of the main 0.6 version because the 0.7 series has Lan Sync.
4) Have multiple computers, use all of them. This is the best way to minimize downtime. Plus, with lan sync enabled DropBox, rebuilding a DropBox from scratch is a lot faster.
5) Use free software. This gets you back on your feet faster. Free software is usually small, easily available, and fast to install. One trick I do is I bookmark the download pages of software I like and tag it “installthis”.
6) Use “portable” software. If you have the option, get programs to run in portable mode. All the datafiles are contained, and not spread out in 4 random hidden corners of your hard drive. They don’t depend on the Windows registry. I use keepass, putty, notepad++, foobar2000, and some other small utilities in portable mode.