If I put enough time (& money) into my step son, will he experience sharp improvements?

I like JHS’s suggestions too. I would say though that IF he ends up the year with a strong grade in Algebra 2, he might consider doing pre-calc/trig in the summer. It will depend on your school system if this is a viable option, but in our school there were always a handful of kids who did this so that they could take calculus sooner. They were usually the strong not the weak math students, so this is only an option if he seems to be on a solid basis by the end of the year.