Abby,
It's clear that you have a strong personality (there's nothing wrong with that!) and a pretty concentrated focus on the key areas of life that matter to you. This is evident from the dominance of planets on the western side of your chart. That exclusive focus, coupled with a strong 1st house (including a Sag moon and SN), means you have a strong independent streak in you, with a touch of missionary zeal.
At the same time, it's clear that the biggest life lessons, and critical turning points in growth, will come through the area of relationships. Not friendships, but intimate relationships and partnerships. With your Chiron and NN in 7th house, this will be an area of pain for you at times. But as you learn to objectively appreciate different points of view (your NN calling), you will gain more inner balance. All of this will start to make sense in the next 2-4 years (if I remembered your age correctly) as you begin to realize where you want to be in relation to where you are at the moment.
Re your Jupiter influence in the first house.....this can manifest in many different ways. One thing I've noticed among a few friends is that it makes them just downright good people. Very ethical, fair, and naturally "jupterian" in how they meet the world. One friend, who has a cancer asc with Jupiter in the first, has really big boobs. (It's actually a problem now.)
Another thing to keep in mind is your transits. You are still really young. There's a lot of life to live and you will be a different person in a few years, then again in another 10-12 years. You will have a stronger sense of purpose and direction from your experiences and relationships between now and then. Our natal charts get activated and we learn a lot of these inner "aspects" and energies as they are brought to the surface for reckoning from transits. Wait until after your 3rd Jupiter return, your nodal return, your Uranus opposition.....it'll all start to fall in place in your head.
You've lived through Saturn transiting your first house, and now it's working it's way through your second, the area where Pluto has already stripped you to the core. This is your house of earned income (net worth), but also the house of your self-worth. Sound familiar? The questions you are asking about income and "luck" are the very things that Saturn is making you consider in a serious, saturnian, way. Saturn wants to make it real....blow away the illusions (Neptune in 2nd) or weak structures and give you the chance to really understand your real worth. The process of going through this can be painful. But it doesn't last forever and it does produce meaningful lessons that allows you to strengthen your chart (yourself) as we live it.
In a nutshell, I would say to ease up a bit on yourself. It's a tough time when these outer planet transit key areas of your chart. But it doesn't last forever. And you've got transiting Jupiter on your side for several years as it supports your inner planets, along with the coming years when it will pass by these very houses that are causing you concern.
I recommend focusing on understanding the 12th house and Neptune. I'm sure you've done that, but Neptune and the 12th is really a complicated area that deserves a lot of thought and objectivity to understand clearly, then translate that understanding into a practical and grounded reality. I see a reoccurring natal theme that places a lot of emphasis on your 12th and Neptune. Study these aspects, the mundane and spiritual meaning of the planets and the houses, and trace over how rulers link to one another. It's clear that you are set to master your 12th house, Neptune energies, and relationships. Your relationships will teach you a lot of these lessons, as evident with Chiron and NN in your 7th house. But with your Libra sun and strong pull toward your SN, it may not always feel comfortable. But the goal here is to be more confident in knowing your worth and more assertive in defining what you deserve in partnership....all in a concrete, unshakable, saturnian way. And from this you'll create a similar increase in the real world like your 2nd house of net worth. But again, it's gotta start with understanding that Neptune influence in your 2nd house and your 12th house presence. Where we have Neptune in our charts is usually where our vision is the most idealistic and possibly lacking in reality. Saturn wants you to get a good saturn grip on it (like turning water into crystal).
While you may not see the "luck" in your life when considering your income, this is because you are undergoing big transits that are forcing you to reckon with this area of your life in a meaningful way. But if you look deeper, you see it's the deep Sagittarian knowledge and faith that will give you the inner tools to make these mental/spiritual connections so you move upward and onward. So your "luck" is definitely a part of you....you're just not seeing it in yourself right now.
Hope I helped?
S.
