I'm not sure if you're just thinking out loud or asking for inputs and insights. These are questions that only you can answer. The good thing is that you have questions to use as starting points, instead of just a nebulous confusion that you cannot articulate.

Probe deeper. For example, what specific qualities do you find attractive in the "type" of women you've been dating recently? How do these women make you feel? What are the reasons you feel unhappy with yourself? Is it possible that by dating women who aren't conventionally successful by your standards, you feel relatively more successful and get a confidence boost? (I'm not suggesting that this is the case). What milestones/flags would help you to assess whether or not you are ready for commitment? (for example, some people might not want to commit until they are financially secure by their own standards; others might want a partner with very specific qualities.)

These are the types of questions you can ask yourself. You can break down the macro questions into smaller parts that can be answered more concretely, and with evidence. It might also be helpful to see a therapist. Professional counselors are trained to ask probing questions and can apply techniques that can help you ask deeper questions yourself.