Personally I have few problems representing geometry because I write scripts calling either one of my own ways of representing geometry (my main interest is numerical simulation not engineering drawings) or, increasingly, the Open Cascade geometry engine which is one of the small number of "industrial strength" geometry engines. CAD packages tend to wrap one of these geometry engines and implement a subset of the capabilities in their own GUI way of doing things. An effective way to bypass many of the limitations of CAD packages is to work with a geometry engine directly using a script. It requires the user to be comfortable writing scripts and working at a lower level closer to how geometry is represented mathematically. It is not the best solution for everyone but it can be open, free, flexible and reliable at the price of some operations being less easy for a user. What seems to be happening now is CAD scripting packages are starting to appear (e.g. OpenSCAD) that wrap a geometry engine with their own limited and proprietary scripted way of doing things that is presumably intended to be easier for the user.
The history of CAD is a pretty weird one given how simple and straightforward the underlying task is and how overly complex CAD software tends to be driven by considerations such as how to gain and keep users, how to make large sums of money,...