Q: I still own a 1st gen iPad; now it won't connect to itunes 11 properly or transfer photos; is it time I upgraded?

there are some things you could do before being sure the iPad needs repair

1, Try on another computer. If you're able to import photos on another computer. In that case, you could try removing and reinstalling iTunes and its components using http://support.apple.com/kb/ht1925  for windows XP or http://support.apple.com/kb/HT1923 for windows Vista or windows 7.

2. Try using another cable

3. If you're not able to import photos on another computer and another cable, the device may need service

Hope this helps

Stijn

iPad not appearing in iTunes

http://www.apple.com/support/ipad/assistant/itunes/

iOS: Device not recognized in iTunes for Mac OS X

http://support.apple.com/kb/TS1591

iOS: Device not recognized in iTunes for Windows

http://support.apple.com/kb/TS1538

IOS: Syncing with iTunes

http://support.apple.com/kb/HT1386

Apple - Support - iPad - Syncing

http://www.apple.com/support/ipad/syncing/

ITunes: Syncing media content to your iOS devices

http://support.apple.com/kb/ht1351

Another way. You can use a USB flash drive & the camera connection kit.

Plug the USB flash drive (works the same with an SD card) into your computer & create a new folder titled DCIM. Then put your movie/photo files into the folder. The files must have a filename with exactly 8 characters long (no spaces) plus the file extension (i.e., my-movie.mov; DSCN0164.jpg).

Now plug the flash drive into the iPad using the camera connection kit. Open the Photos app, the movie/photo files should appear & you can import. (You can not export using the camera connection kit.)

Using The iPad Camera Connection Kit

http://support.apple.com/kb/HT4101

Secrets of the iPad Camera Connection Kit

http://howto.cnet.com/8301-11310_39-57401068-285/secrets-of-the-ipad-camera-conn ection-kit/

 Cheers, Tom