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Will the latest release properly upgrade the database to the newer version? Will the licensing system allow me to do a dry using a different domain just to test everything out?
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You need to stay within your own domain but here is how to achieve developing a test site.
If your V2 site is
www.mysite.com/classifieds, then setup another directory called
www.mysite.com/test - upload all the V3 files there.
Next, setup 'another' MySQL database
Now copy your V2 dB and import it to your new V3 dB.
Copy the 'photos' and 'thumbs' directories from the V2 site to the new V3 site.
Via administration/install, install the script and dB tables.
Now check out your new site and make custom changes to layout.tpl.php
Whilst you are doing this, your original 'classifieds' site remains to function independant of the new test site.
When you are ready, you can then delete the original site and rename your 'test' directory to 'classifieds'.
Hope this helps.