Now. When else? contracting is good for establishing boundaries, because it costs money to violate them. Price according to value of life mission opportunity cost, and have faith you’ll always have enough resources.

No need, the pay for software development is more than enough (like, 3-4x more than enough). The main problems are excess housing prices (so that income is not enough), and a combination of ambition / competitiveness / fear of missing out / fear of running behind.

Have you ever noticed how nobody complains about "excess housing prices" when they can easily afford it and the populations that have been living there for decades can't?

Start writing about it. Five or so years later, if you gain a following, it can have an effect.