Paul, definitely ask your meditation teacher these questions. These boards are just barely better than nothing, it's so much better to talk with a person who knows the details of your practice and can provide fine-scale suggestions.
Just a large scale observation: can you see how your practice is motivated by aversion, greed, and indifference? Not wanting dark night symptoms, wanting juicy metta practice, indifferent about vibration-less meditation states? Paradoxically, the way "go beyond content" is to go right into the content and notice the universal patterns of aversion, greed, and indifference are the context-independent causes of having problem with the specific content that appears in awareness. (That's quite a sentence, hopefully you get my point!)
If you can sit and notice all the ways you make your meditation a problem... then maybe you might notice that the flip side view would be: Oh, I can be interested in investigating dark night symptoms to see how they are created. Oh, I can allow metta to be what it is and simply doing it without expectation. Oh, I can recognize that vibration-less meditation states are as "real" and "worthy" as any other state, maybe I'll let myself hangout and just enjoy the simplicity of that state.
In a sentence: you're trying too hard!
Conventional practices to find happiness are all about prefering one state to another and rejecting the bad one and going toward the good one. But the happiness found in meditation is making peace with all states --- profound equanimity --- while gently allowing practice to deepen -- by innate wisdom, not calculated cunning -- over time.
Keep working with your psychitrist. In many ways, you are still at the stage of building a foundation for deep meditation practice. Allow meditation practice to be a place where thoughts and concerns just "bubble up" and you notice them as simply thoughts and concerns. It's almost like you are learning to be your own therapist, listening to the inner thoughts and concerns, acknowledging them without judgement. Meditation practice at this stage can be like saying to yourself "interesting, tell me more" and then just noticing the contents of your mind.
There is no value in trying to rush through meditation to "get to" stream entry. Stream entry happens when we are just very present and accepting of what occurs in mind without preference or control. If stream entry is your goal, practice accepting whatever occurs in mind without greed, aversion, or indifference.
Your practice will take its own course, according to what you need to experience. It will be different from everyone else. So let it take its shape and customize it to work for you. But don't try to force particular states or insights, it just doesn't work that way. Lots of gentle, low-effort practice is what makes deep changes happen. Using willpower and a lot of effort is actually just training the conventional mind and doesn't lead to resiliance sense of happiness -- it's just more striving, more samsara.
Hope this helps! I'm honestly trying to prevent a lot of mistakes that I myself made

Best wishes.