The "Consultants and Freelance Developers" seems to cover two different aspects:
  1) list devs that are consultants or freelance developers for a living;
  2) list devs that are available and can be hired to work on short term projects;

The second aspect seems orthogonal to the rest of the section (I could be working as educator/trainer, but also be available for short term projects).

IIUC the main goal here is to disclose who are we working for (if any).  However, unless I'm misunderstanding, you also want to have a list of core developers that might be available to do paid work.  ISTM that this paid work could cover at least 3 different categories:
  1) work that won't directly benefit CPython (e.g. a company can hire me as a consultant for one of their project);
  2) work that will benefit CPython (e.g. a company can pay me to add an approved feature/bugfix to CPython);
  3) work on CPython paid by the PSF (e.g. the PSF can pay me to implement a PEP or to work on the infrastructure);

I'm not sure if this was your intention, but if it was, I would put it in a separate section.