Should I use brew or pip for installing matplotlib?
I recommend using a package manager (brew, indeed, or MacPorts). Here are a few reasons why:
If you use your package manager (MacPorts, brew,…) to later install additional programs that depend on Matplotlib, the package manager will install it regardless.
If you install a Python package via pip, and pip installs it in your package manager tree (MacPorts, brew,…), the package manager might complain. For example, MacPorts does not want to erase pip-installed packages, as a precaution, so compilation stops when MacPort detects that someone walked on its turf. The best way of installing Python packages is to first check if they are provided by your package manager, and then only install them with pip if they are not.
Compilation with pip sometimes fails where a package manager (MacPorts,…) has no problem: package managers are simply more powerful and general tools (they play nicely with required compiled libraries, for instance).
I would not recommend using a separate distribution of Matplotlib, for the same kind of reasons: any program from brew that depends on Matplotlib will install it anyway. Furthermore, if you instead want to install such a program without your package manager, it is generally hard to make it work with a specific distribution of Matplotlib (they might need libraries to be installed of top of it, etc.).
In summary, I would recommend to use one system for everything (brew, since this is what you chose), and pip
for things that this system does not provide (just make sure that the pip you use corresponds to where you want things to go: your package manager's Python library, with the right version, or the OS-provided Python,…). Multiplying tools and installs is too messy, in my experience, as various distributions/package managers/etc. are usually not meant to play well with each other.