It is not a problem with the software, pricing is more difficult as value is subjective and only measured against a subset of what the software can do. Communication is probably something that could be improved. Whereas many companies use an update promotion to get users to upgrade it is usually communicated better than "It's coming soon......very long pause" then Suprise discounts for upgrades, "oops too late, tough luck". The v 9 release took 23 months to get to 10 so this was easy to miss.
The value of the cloud sharing licensing still needs clearer detail to differentiate itself from Sketchfab, Matterport, Augment etc.
So look at how some of the CAD software you support handle upgrades
IronCAD the upgrade price is the same no matter what version you upgrade from.
ZW3D - the same upgrade price from any version,
Rhino3D - the same upgrade price from any version
Alibre - the same upgrade price from any version
ZBrush - All Upgrades have been free since version 2
All the Autodesk products are subscription-only, but reasonable value is apparent
Solidworks/Solidedge/Creo - different price category
Onshape is pretty terrible value subscription only.
Modo is maintenance or subscription