Currently, Transmit a Model offers many valuable opportunities for our work, including upgrading models. However it is very easy to make the wrong selections with the check boxes, potentially/accidentally loosing views.
On the negative side, the Workset Display Option gets changed to SPECIFY. I personally like this setting but it may cause problems with novice users who do not understand the workset dialogue will now appear every time they open the model. The panic in their eyes and voice when they believe they've "lost their entire model" is priceless. However ...
My suggestion is the addition of a single button to upgrade the models, with no other choices and offers no other actions, except to upgrade the models. Will simply pass through the current settings, families, etc. in the original models. No purging, no changes to workset display ... no changes! Just upgrade the Revit version.
However simplistic, I believe that this will greatly help the less-than-expert Revit users out there.