First priority is an ample emergency fund, then your wife's debt and your debt. Taking care of this will buy you some time to sort out your way on the rest.

You need to work on finding and building healthy boundaries with your family. Adults made choices, and part of learning life's lessons involves learning to make different choices when things go difficult. Giving too much 'help' to people teaches more dependancy. It will take you to a place where your role with your parents and you get reversed. This is what having money does when misused.

Growing up in an alcoholic home changes people and family dynamics for both good and bad. Among the problems is boundaries and over developed sense of responsibility. I get what you are talking about trying to find balance and feeling privilege family guilt. I grew up this way, too.

My answer was to try to foster independence, resiliency and paths for others to make their own way. If money was given, it was for these results in mind, but not to enable others to stay stuck in their same pit. I had to let adults be adults and live with their choices about work and money without entangling myself greatly in it. I would 'lend' reasonable amounts, but consider it gifts. I also had to make some selfish feeling choice to make sure my children would not want by my trying to assuage my own baggage with money to my parents.

You are right questioning what you should be doing, why you are doing it, and you are very right that giving too much will not help those who want to stay where they are, but will rob you of your future dreams.

This is an area that belongs in relationships, but emotional investing and spending are integral to how money is used. It can make or can break people. Use it wisely.