Thanks for the feedback, at least now I know it's not just me experiencing this.
Wasn't sure if my removing packages and lib's might have done some damage.
In an effort to install Wine I downloaded directly from WineHq and attempted a build which worked but soon uninstalled that then tried the Sid repository, thinking that Sid was a much better approach. I finally gave up on Wine altogether, it's still pretty clunky and crude and, no doubt, why it's not in the testing or stable repositories.
Reinstalled LMDE today and will upgrade to Incoming once again for a fresh start. I'll just go with VirtualBox instead of Wine, much more polished and is a much better fit.
Hope the button issue gets fixed but it's really not a big deal as long as the green icon still indicates that all is well in the repository department.