invoking pip as a possible side effect of installing a weewx extension has "danger will robinson" and "there be dragons" written all over it.
although it *could* mean one fewer step when installing a weewx extension, and it probably would not be a problem on a system that is running only weewx and where weewx was installed using pip and where weewx is being run in a virtual environment (and i might have missed a few more 'and's), it could be problematic in many other situations.
pip is horrible at dependency management - it will happily break one python package as it tries to satisfy dependencies for another, and unless you have extensive unit tests for everything you ever want to run, you won't notice it until something that used to run just fine breaks.
i wish there were a good solution to python installation/upgrade/management that works across operating environments and packaging systems.