1. I agree intuition can be a very useful tool ... as long as negative emotions and thinking don't cloud it. I'd be inclined to give this new T a second chance but make it a priority to determine if her approach will be a good fit for you. Extend your antennae, so to speak. I imagine some Ts use an exaggerated soft voice and approach to soothe clients' anxieties, but it may be her natural way of communicating. If she uses a supportive but not very goal-oriented approach and that's not a good fit for you, speak up about that. State your therapeutic hopes and expectations clearly, and see how she responds. That will clarify things for both of you.
2. Regarding your friend, perhaps living the high life is an anchor for her that helps keep feelings of depression and low self-worth a little more tolerable. I'm not glorifying it, just making an observation. She's wrapped up in her own thinking, so obviously doing that endless rumination process.
At some point you'll have to either keep on avoiding her, or call her out on what's going on. The latter course, if handled with compassion for how she must be feeling right now, seems like the better one to me.
3. Intuitive yet not trusting yourself ... I can relate to that. Possibly it is the fear of making a mistake and thinking of oneself as an error-prone person that does this. What I am learning to do is recognize that sooner or later, you just have to take action, make a decision and stick with it. If it's the wrong course, there's always the potential for learning and therefore making better decisions down the line. It's no good to remain stuck in neutral preparing to decide or take action for too long, that only adds to anxiety, I find.