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Check your Windows user Libraries
Documents, Music, Pictures, Videos and also Downloads
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Check the MRUs of your common apps
The "most recently used" lists, usually found on the file menu of applications such as the
Microsoft Office suite, Textpad, Photoshop, Audacity, etc.
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Desktop
My desktop is always cluttered. That goes for my real ones too :)
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Saved games
I haven't played a big PC game for years, but I'm sure you can still backup the save files. Also watch out for premium
downloads you've paid for. Most of these use activation keys, so search your e-mail.
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Export your e-mails
You're on your own here. All I know is Windows Live Mail doesn't scale.
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Save your web bookmarks
For IE copy the Favorites folder; for Firefox copy bookmarks.html from your profile.
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Repeat all the above steps for other Windows accounts
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Search all hard drives for the types of files you normally work on
For me this is *.tcl, *.html, *.php, *.sql, *.java, *.doc, *.psd, *.jpg, *.png and *.flv for me, but you might have Excel spreadsheets, music files, etc.
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iTunes
You can either backup your entire music library, or just purchases. My apps and bought songs are big enough, so I just backup those and manually copy my ripped mp3s. As of iTunes 10 (iCloud coming soon) you can only backup to DVD or CD,
and if you need multiple discs it might not recognise a DVD after the first disc (I just went through the pain of 1 DVD and 5 CDs). Also you might want to deauthorise your old iTunes as you can only have 5 separate installs.
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Scan through your Program Files and Program Files (x86) folders to refresh your memory
There might be shareware programs whose installation files are still hanging around, for example.
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Stored passwords
Might be in a password vault application, or a text file. Also your browsers, for example Firefox lets you view (but not export) your saved logins. Go to Tools -< Options -< Saved Passwords...
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Sneaky configuration files...
...like the syntax files for Textpad that live in the system folder where ever Textpad was installed.
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Certificates
You might have digital certs for banking, Revenue, Companies Registration, e-mail, server logins, etc.
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Networking
You might want to make a list of what LAN and WiFi networks you can connect to, or remind yourself of your settings for your 3G dongle.
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Hosts
If you have a network might need to keep windows\hosts.
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Proxy settings
If you're behind a firewall it's worth noting the settings for your browser.
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System properties
If you're doing a reinstall on the same hardware it's handy to get an export of the system properties.
Click the Windows button and search for msinfo32. This tool lets you export system settings.
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Fonts
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You'll just die if you can't print your CV in "Groovy70sFunkSoulFontMan".
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Serial Numbers
For those of you who have misplaced your official documentation/cd box, you can sometimes get the serial number of applications
that use them in Help\About. Also search your e-mail if applicable.
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VMware
If you have any virtual machines on your PC, either copy those or go through this whole process
for them also. Speaking of VMware, consider a complete clone of your current version of Windows, or an import
of important data like your e-mail. That way you can refer back to old stuff from a virtual machine
on your new installation.
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Rips / Disk images
If you rip CDs, DVDs, or have other software that uses large disk images, check for these files.
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Partitions
Don't forget the other partitions on the disk, especially if you have a dual boot setup.
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