Free Transform resets frame after each use
If it was the only problem... Have you ever tried to "free transform" an object like you can do it with Photoshop in a breeze ? Free Transform tool (Free Distort) resets the handles to the rectangular bounding box after each handle drag! Super convenient to adjust a deformation! But did Adobe internally have the distortion tools proposed in Illustrator tested? there are 3 or 4 but all are tedious to use and very incomplete. Please, Adobe, put all this in the trash and replace these useless things with a single tool effective and intuitive... exactly like the "free transform" of Photoshop! Speak to real graphic designers and they will show you how to make real tool!
Illustrator today properly keep the Free Transform frame deformed after each use, until you destroy the group it creates.
If you still have problems with the way it works — please comment back.