Problems with current implementation:
+ If user used "Ask me on attempt to upgrade" option, he need to pass through one more dialog (it asks for SVN version) to check out.
+ If user used one of the two options, "Never upgrade" and "Upgrade automatically" and he want to use the opposite option, he need to remember to apply it before checking out
+ User cannot know the version of working copy he will work with at checking out time (if he doesn't remember the version option he saved)
Solution:
Put SVN version option to check out is "SVN Checkout Options" dialog. You can add 2 radio buttons for SVN versions (1.3 and 1.4). When user change the version option, it will be saved somewhere and used for the next time.
Advantages:
+ Group all settings relate with SVN version to one place
+ User doesn't need to remember anything
+ User will know exact version he will work with at checking out time
Disadvantages:
+ Zero