Jeff,
It is very kind of you to volunteer to assist in developing an application, or plug-in by public suggestions. So, thanks for your generosity!
Perhaps it would be prudent to first identify a general direction for the scale, and scope, before we get lost in the weeds trying to be overly specific... To build a stand-alone application to function outside of AutoCAD, or to build a plug-in to function within AutoCAD?
IMO, there's more to be gained, and more users that will participate in the debugging, etc. if we go with the latter. A plug-in also allows for generalization in that we can develop a plug-in that is supported across multiple platforms (i.e., Vanilla AutoCAD, and verticals alike)... hopefully.
Generally speaking, there's a ton of things that can be done, or at least refined.