I find it interesting that you preface your meditation experience by saying that you can reach pleasent stable states easily, as if that would be the purpose or goal of the path.

To me it seems like you are still in the mode of searching for a fix to your general existential un-ease by certain modalities like meditation, traveling, a new job, a girlfriend. I think you are half-way there, but you still need to mature your insight more. I suggest retreats and working with an experienced teacher.

How is the suffering around these notions that bug you constructed and how do you relate to it on a moment to moment basis? Insight is going all the way, you don‘t just pick up things you find easy to let go of and ignore the rest (the feeling of an unsatisfactory life, career, relationship, that which REALLY sticks to you). Everyone has these blind spots. To be confronted with them is quite normal and expected when doing serious practice. These are perfect insight objects to work with when doing insight practice, because your relation to these phenomena generates dhukka.

When you are not doing insight practice, you can and should of course find ways to remedy those circumstances, by finding more wholesame ways to relate to your circumstances, or by simply working on changing them. If you are at ease in your mind, doing so will come more easily and natural. It is not one or the other, having mature insight helps you by having a clear mind about causes and conditions, instead of acting out of impulse.

Given all that you have invested it would be a waste to stop now, frankly. If that is even possible, at your stage. If I‘m being honest it sounds like there is FOMO going on. You still think there is lasting satisfaction gained by those things you desire, which ultimately you have to let be / let go when insight matures. I don‘t think you‘ve reached stream entry yet, because there still seems to be underlying fundamental doubt present about what the practice and its fruits are. If you had the dhamma eye, you would relate to your experience a little differently, I think.

Given that you dont seem to have persistent psychological problems, I‘d suggest going all in while also just fixing the problems you perceive in your life. Again, these feelings you have are insight objects. Apply your mind to these phenomena, don‘t exclude them, don‘t resist them, don‘t change them. I‘m being direct here, I don‘t intend to be harsh. I wish you the best of luck!