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Your version of Resco Explorer will be flakey, but you should not need to buy an upgrade! Minor revisions, like v5.20 to the new v5.30 will not cost you a dime and will just use your current registration. That policy is on Resco's site under support.
Your version of Photo Viewer is the latest and works OK under WM5.
Yes, I run both on my X51v with WM5.
Pocket Streets will run fine under WM5 too.
Good luck!
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