^ good advice Ali… you seem to also support the first of two options I had noted in my first post.
FairyTale, your brother is at an age and juncture where he is going to get wrapped around in second guessing himself as well as what others tell him. The best way to alleviate this is to have enough information on hand to be able to make a decision, and you’re certainly helping him in that respect. Secondly, once you have the choices figured out, line them up against objectives and value you seek out of those decisions. A simple pros/cons list along with a discussion of future course of action can often help reach resolute decisions.