It sounds like you two share some traits, so it seems like being honest about your feelings might be somewhat low risk. If you both have depression and some form or anxiety, she might be having similar feelings. It could be that, while you go along as a coping mechanism, she blurts out what she’s thinking to the same end.
In the end, if you value your relationship with her, honestly is always the best policy.
I was listening to Behind the Bastards and the guest asked him why it seems like there’s a pattern of crazy wealthy people doing sex pest things. He said there was a study that related a certain level of wealth to having a brain injury. Basically, when you have a certain amount of crazy obscene wealth, the concept of value loses all meaning to you, and that loss affects other types of value as well - like personal value. Wish I could find more about that. Seems like it would be an interesting read.
That said, I would take my unlimited money and build an underwater Bond villain lair. From there I would do what I could to make the world better, but leave me alone.