Hi, I am a couple years younger than you, (ironically had a birthday the day you posted this thread) and I have this placement. Of course, other chart placements will colour the mamifestation of this conjunction so bare that in mind.
Hard to say if my experiences would classify as positive, but reading your description it would seem that I have a bit more control in that department. I am neither passive, nor passive aggressive about earning my own money. I am the opposite -- very aggressive and proactive about sustaining myself. I have been classed as a workaholic, always cognizant of the dynamics involved in services rendered, and always looking for greater opportunities to earn more. I also have very strict boundaries when it comes to money/finances, and nobody is allowed to take advantage or pressure me into compromising situations unless I am completely above board and accepting of the idea to help/assist them. I give 0 ****s about consumerism, and most purchases are in service to achieving goals either directly or indirectly.
I am not a rich man, and due to a lot of unlucky and negative circumstances I have had to start from scratch. This has only bolstered my "gameness", as I am naturally attracted to challenges and difficulty. I have "potential" that I am trying to convert into something realistic. Despite the obstacles, I have been able to keep myself afloat, pay for school (trying to change my career trajectory), invest (not stock market), and save. I have recently been thinking about using "good debt" to get ahead, as I have yet to utilise credit in any fashion (I am not a US citizen where credit is ubiqitious). My "balance sheet" is decent -- nothing spectacular but I am not drowning or behind on anything, and am still able to spend on something luxurious once in a while.
I would say that Mars conjunct. Jupiter in my case increases the desire to be proactive and entrepreneurial. I have all my planets on the left side of the chart, so this increases the tendency toward self-sufficiency. Bundle chart people are supposed to be good at managing limited resources and I think Moon in 2nd makes it important for me to be financially sound in order to have some emotional equilibrium, so I am going to be focused on doing and knowing the things that contributes to those outcomes.
With regard to your chart, there are some concerning placements that may contribute to negative 2nd house outcomes. You have the Scorpio to Aquarius squares from the 12th to the 2nd that ties in 12th house themes with 2nd house themes. Couple the fact that these discordant aspects are comprised of the traditional malefics, and we see that you have a bit of a uphill climb with regard to your financial problems.
Have you ever tried to learn financial literacy? There are ample resources online in both video and text format. Another thing I am wondering is, what is it about earning your own money that is distasteful to you?
Oh, I will add that in the past there has been some "financial co-dependency" as you call it, as family members who were intelligent and able bodied sought to parasite on me, causing a net negative in quality of life for all involved. When the time came, it was easy for me to cut them out of my life and my only regret is that I should have done it sooner.