I think both situations are unsustainable. I'm not financially stable because I hate my job and might quit at any time and he doesn't make enough money.

But I think my main point is both of us have a way of becoming sustainable so you might as well do what makes you happy instead of working a job you hate for 8 years. Being a waiter making 40k isn't enough long term, but working your way into a higher end establishment or management is. A girl I dated started out as barista, became a store manager, and is now the regional manager and makes ~125k a year and more importantly she is a perfect fit for the job and enjoyed it the entire time.

All I'm trying to say is there are a lot of paths to a sustainable life even when following your natural inclinations.

But anyway OP responded his son's not super interested in college anyway so his plan sounds good to me anyway.