Using IDEA 5.0 #3425 on windows XP Professional
Check "Skip this dialog" in the Check Out dialog form causes the Checkindialog form to be hidden.
To reproduce connect project to source safe. open a file that is in Source Safe and press cursor inside and try to edit. The Checkout dialog appears click on "Skip this dialog" and checkout file. Make chagnes and try to checkin and you would not see the checkin dialog. Try to check out another file and you still see the checkout dialog.