So I finally had one of my websites (out of 8 on the same server) start experiencing the Edit Mode issue, though mine was different, it actually would prompt me with windows auth to login after clicking on the EDIT MODE button.

Here's what I did to resolve it

My site was in a folder called wwwroot
I made a copy of that folder
I renamed the copy to wwwroot2
I pointed IIS to wwwroot2
had to do some hard refreshes, cache issues otherwise
now my site works fine
tried some fancy renaming, changing WWWROOT to wwwroot_old, and wwwroot2 to wwwroot, but couldn't get it to work
anyways, the site works now with IIS pointing to WWWROOT2.

I can't explain it, but I've spent the last 4 hours trying to resolve this, and this was the only work around I could get going.

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Chris Hammond
Former DNN Corp Employee, MVP, Core Team Member, Trustee
Christoc.com Software Solutions DotNetNuke Module Development, Upgrades and consulting.
dnnCHAT.com a chat room for DotNetNuke discussions

i have to use this fix constantly for each new instance of 7.nnn i use on my 2008r2 webserver.
thanks for the pointer