Thanks for bringing your question to JustAnswer.
The very fact that you're asking this question suggests that you're realizing that your new counselor is not "walking her talk." As a self-proclaimed expert in ADHD, she should have the tools to be organized, remember your homework, etc. Her missing many appointments is appallingly unprofessional.
Also, making judgments about your significant other is not appropriate for a counselor. She should be exploring your feelings about him, not offering hers.
The fact that you know that she is struggling financially --something no client should ever know about her counselor--means that she is violating boundaries in more areas than passing judgment on your boyfriend.
It really, really isn't your job to help support your counselor.
And by the way, the fact that she's encouraging you to get disability does not mean you will actually get it. If ADHD is your main diagnosis, the chances are almost non-existent that you will get it. With all the people out of work these days, the applications to disability are skyrocketing....and so are the denials. The only folks getting mental health disability these days are the significantly disabled. So even though it might be pleasant to hear her say "go for it" ...that doesn't mean that you have a factual , actual chance of actually getting it. Make an appointment with a disability lawyer, and see what they say your chances actually are. (People with Bipolar I or Schizophrenia have the best chance of getting disability).
Perhaps it's time to re-visit your original counselor, and be up-front about wanting to be challenged by her. If you aren't able to reach an agreement about what "being challenged" means, then start the search for yet another person. Your current therapist only seems to be challenging you by not showing up for appointments and expecting you to deal with her personal issues...